2-Hydroxypropanehydrazide → 2-chloro-4-(o-chlorophenyl)-9-(alpha-hydroxyethyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine

HRID 262992Notes

Reaction equation

HRID 262992 reaction equation
[Cl:1][C:2]1[S:19][C:5]2[NH:6][C:7](=S)[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.[C:20]([NH:25][NH2:26])(=O)[CH:21]([CH3:23])[OH:22]>CO>[Cl:1][C:2]1[S:19][C:5]2[N:6]3[C:20]([CH:21]([OH:22])[CH3:23])=[N:25][N:26]=[C:7]3[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 3120432-HydroxypropanehydrazideHCID 1357830787-Chloro-5-(2-chlorophenyl)-1,3-dihydro-2H-thieno-(2,3-e)-(1,4)-diazepine-2-thione

Product 1

HCID 213176752-chloro-4-(o-chlorophenyl)-9-(alpha-hydroxyethyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 g of 7-chloro-5-(o-chlorophenyl)-1,3-dihydro-2H-thieno[2,3-e]-1,4-diazepine-2-thione is refluxed for 1.5 hours in 50 ml of absolute methanol with 2 g of lactic acid hydrazide. The precipitated 7-chloro-5-(o-chlorophenyl)-2-(2-lactoylhydrazino)-3H-thieno[2,3-e]-1,4-diazepine is dried and refluxed for 4 hours in 120 ml of absolute xylene. The solution is evaporated and the product recrystallized from ethyl acetate containing active carbon to yield 2-chloro-4-(o-chlorophenyl)-9-(α-hydroxyethyl)-6H-thieno[3,2-f]-s- triazolo[4,3-a][1,4]diazepine of melting point 118°-120° C.

Workup

  1. dry with materialThe precipitated 7-chloro-5-(o-chlorophenyl)-2-(2-lactoylhydrazino)-3H-thieno[2,3-e]-1,4-diazepine is dried
  2. temperaturerefluxed for 4 hours in 120 ml of absolute xylene
  3. customThe solution is evaporated
  4. customthe product recrystallized from ethyl acetate containing active carbon

Sources & evidence

ORD record
ord-406a2536ca584892889ddd9beae8b76c
Source dataset
uspto-grants-1979_05
Patent number
US04155913

Reaction notes

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