Hydrogen Sulfide → Methyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]phenoxyacetate

HRID 1900874Notes

Reaction equation

HRID 1900874 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][C:10](=[O:24])[NH:11][C:12]2[CH:23]=[CH:22][C:15]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:13]=2)=[O:8])=[CH:5][CH:4]=1)#[N:2].[SH2:27]>N1C=CC=CC=1.C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10](=[O:24])[NH:11][C:12]2[CH:23]=[CH:22][C:15]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:13]=2)=[O:8])=[CH:25][CH:26]=1)(=[S:27])[NH2:2]

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 23370013Methyl 4-[3-(4-cyanobenzoyl)ureido]phenoxyacetate

Product 1

HCID 23369995Methyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]phenoxyacetate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

A solution of the product of step (a) (850 mg) in pyridine (48 ml) and triethylamine (7 ml) was covered with a blanket of H2S gas and stirred at ambient temperature for 16 hours. The reaction mixture was evaporated to dryness and the residue was triturated with dry ether. The resultant solid was washed thoroughly with ether to give methyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]phenoxyacetate (880 mg) as a yellow solid: NMR Spectrum (DMSO-d6) 3.72 (3H, s), 4.78 (2H, s), 6.95 (2H, d), 7.48 (2H, m), 7.93 (2H, d), 8.06 (2H, d), 9.65 (1H, br s), 10.05 (1H, br s), 10.62 (1H, s).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue was triturated with dry ether
  3. washThe resultant solid was washed thoroughly with ether

Sources & evidence

ORD record
ord-b5693b3bd2404933abe9b36681371d2f
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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