Hydrazinecarboxaldehyde → Estazolam

HRID 1288066

반응식

HRID 1288066 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=S)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1.[CH:20]([NH:22][NH2:23])=O>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:20]=[N:22][N:23]=[C:10]3[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1

참가 물질

4

반응물 2

HCID 12229HydrazinecarboxaldehydeHCID 826706Thionordiazepam

생성물 1

HCID 3261Estazolam

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A mixture of 5.74 g. (0.020 mole) of 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione, 3.6 g. (0.060 mole) of formic acid hydrazide and 200 ml. of 1-butanol was refluxed for 3.75 hours with a slow stream of nitrogen bubbling through the mixture. The mixture was concentrated, the residue was suspended in water, and the suspension was filtered. The filter cake consisted principally of unchanged starting material. The filtrate was concentrated, ethyl acetate and Skellysolve B hexanes being added during the concentration, giving crude product (2.54 g.) of melting point 220.5°-225° C. Recrystallization of this material from ethyl acetate-Skellysolve B hexanes gave 8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine of melting point 228°-229° C. The ultraviolet spectrum (ethanol) had end absorption λ max. 222 (ε = 40,950) and inflections at 245 (ε = 16,200) and 285 mμ(ε = 3,500).

후처리

  1. additionA mixture of 5.74 g
  2. concentrationThe mixture was concentrated
  3. filtrationthe suspension was filtered
  4. concentrationThe filtrate was concentrated
  5. additionethyl acetate and Skellysolve B hexanes being added during the concentration
  6. customgiving crude product (2.54 g.) of melting point 220.5°-225° C
  7. customRecrystallization of this material from ethyl acetate-Skellysolve B hexanes

출처 및 근거

ORD 기록
ord-c195d14230f8426daf2011c549160f8b
출처 데이터셋
uspto-grants-1976_10
특허 번호
US03987052

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