Hydrogen Sulfide → t-Butyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]-3-methylphenoxyacetate

HRID 1900895Notes

Reaction equation

HRID 1900895 reaction equation
[C:1]([C:3]1[CH:30]=[CH:29][C:6]([C:7]([NH:9][C:10](=[O:28])[NH:11][C:12]2[CH:26]=[CH:25][C:15]([O:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:14][C:13]=2[CH3:27])=[O:8])=[CH:5][CH:4]=1)#[N:2].N1C=CC=CC=1.[SH2:37]>C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10](=[O:28])[NH:11][C:12]2[CH:26]=[CH:25][C:15]([O:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:14][C:13]=2[CH3:27])=[O:8])=[CH:29][CH:30]=1)(=[S:37])[NH2:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 1049PyridineHCID 23370039t-Butyl 4-[3-(4-cyanobenzoyl)ureido]-3-methylphenoxyacetate

Product 1

HCID 23369996t-Butyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]-3-methylphenoxyacetate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a similar manner to Example 1, starting material step (b), the product of step (c) (611 mg), pyridine (70 ml), triethylamine (10 ml) and H2S gas were reacted to give t-butyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]-3-methylphenoxyacetate (660 mg) as a yellow solid: NMR Spectrum (DMSO-d6) 1.44 (9H, s), 2.27 (3H, s), 4.61 (2H, s), 6.76 (1H, dd), 6.83 (1H, d), 7.76 (1H, d), 7.95 (2H, d), 8.05 (2H, d), 9.67 (1H, br s), 10.06 (1H, br s), 10.55 (1H, s), 11.12 (1H, s); Mass Spectrum m/Z 466 (M+Na)+.

Sources & evidence

ORD record
ord-4a3ffba019634f21876c4b5d913d4017
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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