METHOD OF SYNTHESIS OF 2-[BIS-(2-CHLOROETHYL)AMINO]-TETRAHYDRO-2H-1,3,2-OXAZAPHOSPHORIN-2-OXIDE MONOHYDRATE
FIELD: organic chemistry, chemical technology. SUBSTANCE: invention relates to organic synthesis, in particular, to method of synthesis of 2-[bis-(2-chloroethyl)amino] tetrahydro-2H-1,3,2-oxaza-phosphorin-2-oxide monohydrate used in pharmacy as an antitumor preparation cyclophosphan. By proposed met...
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| creator | KRIVTSOVA I.JU SOROKINA I.K GOJZMAN M.S ROMANOVA O.B GRANIK V.G |
| description | FIELD: organic chemistry, chemical technology. SUBSTANCE: invention relates to organic synthesis, in particular, to method of synthesis of 2-[bis-(2-chloroethyl)amino] tetrahydro-2H-1,3,2-oxaza-phosphorin-2-oxide monohydrate used in pharmacy as an antitumor preparation cyclophosphan. By proposed method the end product is synthesized from diethanolamine by 3-staged schedule: at the first stage diethanolamine and thionyl chloride taken in the ratio = 1: (2.5-3.0) are boiled in chloroform medium and reaction product is isolated by acetone addition. Isolated product is boiled in phosphorus oxychloride medium and product is isolated by addition of carbon tetrachloride; isolated product is subjected for interaction with 3-aminopropanol at temperature 15-20 C; product of this stage is treated with water and obtained product is crystallized from ethyl acetate at temperature (-5) C - (-10) C. The proposed technology allows to the advanced yield of end product up to 49.4% as measured for the parent diethanolamine and obtain product corresponding to Pharmacopoeia requirement. EFFECT: improved method of synthesis, simplified technology, advanced yield. 1 cl, 1 ex |
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SUBSTANCE: invention relates to organic synthesis, in particular, to method of synthesis of 2-[bis-(2-chloroethyl)amino] tetrahydro-2H-1,3,2-oxaza-phosphorin-2-oxide monohydrate used in pharmacy as an antitumor preparation cyclophosphan. By proposed method the end product is synthesized from diethanolamine by 3-staged schedule: at the first stage diethanolamine and thionyl chloride taken in the ratio = 1: (2.5-3.0) are boiled in chloroform medium and reaction product is isolated by acetone addition. Isolated product is boiled in phosphorus oxychloride medium and product is isolated by addition of carbon tetrachloride; isolated product is subjected for interaction with 3-aminopropanol at temperature 15-20 C; product of this stage is treated with water and obtained product is crystallized from ethyl acetate at temperature (-5) C - (-10) C. The proposed technology allows to the advanced yield of end product up to 49.4% as measured for the parent diethanolamine and obtain product corresponding to Pharmacopoeia requirement. 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SUBSTANCE: invention relates to organic synthesis, in particular, to method of synthesis of 2-[bis-(2-chloroethyl)amino] tetrahydro-2H-1,3,2-oxaza-phosphorin-2-oxide monohydrate used in pharmacy as an antitumor preparation cyclophosphan. By proposed method the end product is synthesized from diethanolamine by 3-staged schedule: at the first stage diethanolamine and thionyl chloride taken in the ratio = 1: (2.5-3.0) are boiled in chloroform medium and reaction product is isolated by acetone addition. Isolated product is boiled in phosphorus oxychloride medium and product is isolated by addition of carbon tetrachloride; isolated product is subjected for interaction with 3-aminopropanol at temperature 15-20 C; product of this stage is treated with water and obtained product is crystallized from ethyl acetate at temperature (-5) C - (-10) C. 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SUBSTANCE: invention relates to organic synthesis, in particular, to method of synthesis of 2-[bis-(2-chloroethyl)amino] tetrahydro-2H-1,3,2-oxaza-phosphorin-2-oxide monohydrate used in pharmacy as an antitumor preparation cyclophosphan. By proposed method the end product is synthesized from diethanolamine by 3-staged schedule: at the first stage diethanolamine and thionyl chloride taken in the ratio = 1: (2.5-3.0) are boiled in chloroform medium and reaction product is isolated by acetone addition. Isolated product is boiled in phosphorus oxychloride medium and product is isolated by addition of carbon tetrachloride; isolated product is subjected for interaction with 3-aminopropanol at temperature 15-20 C; product of this stage is treated with water and obtained product is crystallized from ethyl acetate at temperature (-5) C - (-10) C. The proposed technology allows to the advanced yield of end product up to 49.4% as measured for the parent diethanolamine and obtain product corresponding to Pharmacopoeia requirement. EFFECT: improved method of synthesis, simplified technology, advanced yield. 1 cl, 1 ex</abstract><edition>7</edition><oa>free_for_read</oa></addata></record> |
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| subjects | ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM CHEMISTRY HUMAN NECESSITIES HYGIENE MEDICAL OR VETERINARY SCIENCE METALLURGY ORGANIC CHEMISTRY PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS |
| title | METHOD OF SYNTHESIS OF 2-[BIS-(2-CHLOROETHYL)AMINO]-TETRAHYDRO-2H-1,3,2-OXAZAPHOSPHORIN-2-OXIDE MONOHYDRATE |
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