Ammonia → HCID 178477851, compound

HRID 437937Notes

Reaction equation

HRID 437937 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:14][CH2:13][C:9]3[S:10][CH:11]=[CH:12][C:8]=3[C:7](=[N:15]O)[C:6]=2[CH:17]=1.[Cl-].[NH4+:19].N>[Zn].C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:14][CH2:13][C:9]3[S:10][CH:11]=[CH:12][C:8]=3[CH:7]([N:15]=[C:5]3[CH2:6][CH2:17][CH2:2][CH2:3][CH2:4][NH:19]3)[C:6]=2[CH:17]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 86734897HCID 86734897, compound

Product 1

HCID 178477851HCID 178477851, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

80.5 g of 6-chloro-9,10-dihydro-4-hydroxyimino-4H-benzo-[4,5]cyclohepta[1,2-b]thiophene, 105 g of zinc dust and 14 g of ammonium chloride are stirred with 1750 ml of 25% ammonia solution and 350 ml of ethanol for 3 hours at the boiling temperature. Upon cooling to room temperature, the undissolved portion is filtered off and is washed with benzene. 200 ml of concentrated caustic soda solution are added to the filtrate which is extracted with a mixture of ether/benzene 1:1. The organic phase is washed with saturated common salt solution, dried over magnesium sulphate and the solvent is removed by evaporation. The remaining 4-amino-6-chloro-9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophene is converted in ethanol into the hydrochloride. M.Pt. decomp. from 234°.

Workup

  1. filtrationthe undissolved portion is filtered off
  2. washis washed with benzene
  3. addition200 ml of concentrated caustic soda solution are added to the filtrate which
  4. extractionis extracted with a mixture of ether/benzene 1:1
  5. washThe organic phase is washed with saturated common salt solution
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent is removed by evaporation
  8. customfrom 234°

Sources & evidence

ORD record
ord-0b95675c725a458e8768c19f50042fb3
Source dataset
uspto-grants-1977_06
Patent number
US04032640

Reaction notes

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