Acetohydrazide → HCID 21317685, compound

HRID 262973Notes

Reaction equation

HRID 262973 reaction equation
[Cl:1][C:2]1[S:21][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[N+:17]([O-:19])=[O:18])[C:4]=2[CH:3]=1.[C:22]([NH:25][NH2:26])(=O)[CH3:23]>C(O)CCC>[Cl:1][C:2]1[S:21][C:5]2[N:6]3[C: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[N+:17]([O-:19])=[O:18])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 135848421HCID 135848421, compound

Product 1

HCID 21317685HCID 21317685, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

0.2 g of 7-chloro-1,3-dihydro-5-(o-nitrophenyl)-2H-thieno[2,3-e]-1,4-diazepine-2-thione are heated to reflux for 5 hours under a nitrogen atmosphere with 0.2 g of acetic acid hydrazide in 30 ml of n-butanol. After evaporation of the solvent, the product is taken up in methylene chloride and extracted several times with 1-N hydrochloric acid, the organic phase being treated portionwise with ether such that it comes to the surface in the separating funnel. After neutralization of the aqueous phase with sodium bicarbonate, the mixture is extracted with methylene chloride, the solvent evaporated after drying over sodium sulphate and the residue made into a paste with ethyl acetate. The resulting crystals are recrystallized from ethyl acetate containing active carbon to give colorless crystals of 2-chloro-9-methyl-4-(o-nitrophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine, melting point 210°-212° C.

Workup

  1. customAfter evaporation of the solvent
  2. extractionextracted several times with 1-N hydrochloric acid
  3. additionthe organic phase being treated portionwise with ether such that it
  4. extractionAfter neutralization of the aqueous phase with sodium bicarbonate, the mixture is extracted with methylene chloride
  5. customthe solvent evaporated
  6. dry with materialafter drying over sodium sulphate
  7. customThe resulting crystals are recrystallized from ethyl acetate containing active carbon

Sources & evidence

ORD record
ord-5db022cdd80f4ce1a8f657181c6c5476
Source dataset
uspto-grants-1979_05
Patent number
US04155913

Reaction notes

Loading…