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

HRID 262994Notes

Reaction equation

HRID 262994 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]([NH2:26])(=[O:25])[C:21]([NH:23][NH2:24])=O>CO>[Cl:1][C:2]1[S:19][C:5]2[N:6]3[C:21]([C:20]([NH2:26])=[O:25])=[N:23][N:24]=[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 68200Oxamic acid hydrazideHCID 1357830787-Chloro-5-(2-chlorophenyl)-1,3-dihydro-2H-thieno-(2,3-e)-(1,4)-diazepine-2-thione

Product 1

HCID 706013012-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine-9-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.8 g of 7-chloro-5-(o-chlorophenyl)-1,3-dihydro-2H-thieno[2,3-e]-1,4-diazepine-2-thione are refluxed in 40 ml of absolute methanol with 1.5 g of oxalic acid amide hydrazide for 1.5 hours. The solution is concentrated to 10 ml and left to crystallize in a refrigerator. The filtered and dried 7-chloro-5-(o-chlorophenyl)-2-(2-oxalylamidohydrazino)-3H-thieno[2,3-e]-1,4-diazepine is refluxed in 100 ml of absolute xylene for 3 hours. The organic phase is evaporated and the residue recrystallized from ethanol to yield 2-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine-9-carboxylic acid amide, melting point 248°-251° C.

Workup

  1. concentrationThe solution is concentrated to 10 ml
  2. waitleft
  3. customto crystallize in a refrigerator
  4. filtrationThe filtered
  5. temperaturedried 7-chloro-5-(o-chlorophenyl)-2-(2-oxalylamidohydrazino)-3H-thieno[2,3-e]-1,4-diazepine is refluxed in 100 ml of absolute xylene for 3 hours
  6. customThe organic phase is evaporated
  7. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-7b2433372005426889c12fb1a36cfdf5
Source dataset
uspto-grants-1979_05
Patent number
US04155913

Reaction notes

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