Cyanoacetic acid hydrazide → 2-chloro-4-(o-chlorophenyl)-9-cyanomethyl-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine

HRID 262993

Reaction equation

HRID 262993 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]([CH2:22][C:23]([NH:25][NH2:26])=O)#[N:21]>CO>[Cl:1][C:2]1[S:19][C:5]2[N:6]3[C:23]([CH2:22][C:20]#[N:21])=[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 8820Cyanoacetic acid hydrazideHCID 1357830787-Chloro-5-(2-chlorophenyl)-1,3-dihydro-2H-thieno-(2,3-e)-(1,4)-diazepine-2-thione

Product 1

HCID 213176772-chloro-4-(o-chlorophenyl)-9-cyanomethyl-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.2 g of 7-chloro-5-(o-chlorophenyl)-1,3-dihydro-2H-thieno[2,3-e]-1,4-diazepine-2-thione are refluxed for 1.5 hours together with 2 g of cyanoacetic acid hydrazide in 80 ml of absolute methanol, a dry nitrogen stream being conducted through the solution. The solution is concentrated to 10 ml and left to crystallize. The 7-chloro-5-(o-chlorophenyl)-2-(2-cyanoacetylhydrazino)-3H-thieno[2,3-e]-1,4-diazepine, which is filtered off under a vacuum and dried, is refluxed for 2 hours in 150 ml of absolute xylene. The solution is evaporated and the residue recrystallized from ethyl acetate containing active carbon to yield 2-chloro-4-(o-chlorophenyl)-9-cyanomethyl-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine, melting point 217°-220° C.

Workup

  1. concentrationThe solution is concentrated to 10 ml
  2. waitleft
  3. customto crystallize
  4. filtrationThe 7-chloro-5-(o-chlorophenyl)-2-(2-cyanoacetylhydrazino)-3H-thieno[2,3-e]-1,4-diazepine, which is filtered off under a vacuum
  5. customdried
  6. temperatureis refluxed for 2 hours in 150 ml of absolute xylene
  7. customThe solution is evaporated
  8. customthe residue recrystallized from ethyl acetate containing active carbon

Sources & evidence

ORD record
ord-33d141d1a0e84f5f8f15b4f0fcdec715
Source dataset
uspto-grants-1979_05
Patent number
US04155913

Linked notes

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