ethyl 6-amino-4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]-triazolo[4,3-a][1,4]diazepine-6-carboxylate → 6-amino-4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine

HRID 981460Notes

Reaction equation

HRID 981460 reaction equation
[NH2:1][C:2]1(C(OCC)=O)[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:6]2[CH:16]=[C:17]([CH2:19][CH3:20])[S:18][C:5]=2[N:4]2[C:21]([CH3:24])=[N:22][N:23]=[C:3]12>C(O)C.O>[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:6]2[CH:16]=[C:17]([CH2:19][CH3:20])[S:18][C:5]=2[N:4]2[C:21]([CH3:24])=[N:22][N:23]=[C:3]12

Participants

4

Reactant 1

HCID 15662236ethyl 6-amino-4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]-triazolo[4,3-a][1,4]diazepine-6-carboxylate

Product 1

HCID 156622376-amino-4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepineYield 85.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a mixture of 180 ml of ethanol and 60 ml of water was dissolved 15.1 g of ethyl 6-amino-4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-carboxylate. To the solution was added 6.0 g of crystals of barium hydroxide·8 hydrate, and the mixture was stirred at room temperature for 24 hours. After the solvent was distilled off under reduced pressure, 200 ml of water and 100 ml of benzene were added and the mixture was stirred fully. The water layer was separated, adjusted to pH 2 with 1N hydrochloric acid and left standing still for 24 hours. Thereafter, the mixture was neutralized with sodium carbonate, and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in chloroform and insoluble matters were filtered off. After the solvent was distilled off under reduced pressure, the residue was recrystallized from ethanol to give 10.7 g of 6-amino-4-( 2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]-diazepine, m.p. 130°-131° C.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure, 200 ml of water and 100 ml of benzene
  2. additionwere added
  3. stirringthe mixture was stirred fully
  4. customThe water layer was separated
  5. waitleft
  6. waitstanding still for 24 hours
  7. filtrationthe precipitated crystals were collected by filtration
  8. dissolutionThe obtained crystals were dissolved in chloroform
  9. filtrationinsoluble matters were filtered off
  10. distillationAfter the solvent was distilled off under reduced pressure
  11. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-8f1ef56dda6f4cf28e2af7f5f4e9f43a
Source dataset
uspto-grants-1991_02
Patent number
US04992437

Reaction notes

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