Hydrazinecarboxaldehyde → Estazolam

HRID 1288066

反応式

HRID 1288066 の反応式
[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

参加物

4

反応物 2

HCID 12229HydrazinecarboxaldehydeHCID 826706Thionordiazepam

生成物 1

HCID 3261Estazolam

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c195d14230f8426daf2011c549160f8b
出典データセット
uspto-grants-1976_10
特許番号
US03987052

関連ノート

読み込み中…