Hydrogen Sulfide → Ethyl 4-[(5-thiocarbamoyl-2-benzofuranyl)carbonylamino]phenoxyacetate

HRID 1290995Notes

Reaction equation

HRID 1290995 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([NH:13][C:14]3[CH:26]=[CH:25][C:17]([O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=3)=[O:12])=[CH:8][C:7]=2[CH:27]=1)#[N:2].[SH2:28]>N1C=CC=CC=1.C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([NH:13][C:14]3[CH:26]=[CH:25][C:17]([O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=3)=[O:12])=[CH:8][C:7]=2[CH:27]=1)(=[S:28])[NH2:2]

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 18919414Ethyl 4-[(5-cyano-2-benzofuranyl)carbonylamino]phenoxyacetate

Product 1

HCID 18919404Ethyl 4-[(5-thiocarbamoyl-2-benzofuranyl)carbonylamino]phenoxyacetate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

Ethyl 4-[(5-cyano-2-benzofuranyl)carbonylamino]phenoxyacetate (1.49 g, 4.09 mmol) was dissolved in a mixed solvent of pyridine (50 ml) and triethylamine (5 ml). A hydrogen sulfide gas was blown in for 10 minutes at room temperature and the mixture was stirred for 16 hours. Low boiling matters were distilled away from the reaction mixture under reduced pressure to give ethyl 4-[(5-thiocarbamoyl-2-benzofuranyl)carbonylamino]phenoxyacetate as a yellow solid. Acetone (100 ml) and iodomethane (10 ml) were added to this solid, and the mixture was refluxed under heating for 2 hours. The reaction mixture was heated to room temperature. The resulting precipitate was collected by filtration to give ethyl 4-[[5-[(1-methylthio)iminomethyl]-2-benzofuranyl]carbonylamino]phenoxyacetate as a yellow solid. To this solid was added ethanol (50 ml) and benzylamine (0.5 ml, 4.6 mmol), and the mixture was refluxed under heating for 2 hours. The reaction mixture was concentrated to about 10 ml under reduced pressure, and diethyl ether (40 ml) was added. The resulting precipitate was collected by filtration to give 1.970 g of hydriodide of compound (1) as a yellow solid (69% in three steps).

Workup

  1. customwas blown in for 10 minutes at room temperature
  2. distillationwere distilled away from the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-b634026793f64313b2e3bccfae614f46
Source dataset
uspto-grants-1998_05
Patent number
US05753670

Reaction notes

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