Hydrogen Sulfide → HCID 23370011, compound

HRID 1900898Notes

Reaction equation

HRID 1900898 reaction equation
[C:1]([C:3]1[CH:29]=[CH:28][C:6]([C:7]([NH:9][C:10](=[O:27])[NH:11][C:12]2[CH:25]=[CH:24][C:15]([O:16][CH2:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[CH:14][C:13]=2[CH3:26])=[O:8])=[CH:5][CH:4]=1)#[N:2].N1C=CC=CC=1.[SH2:36]>C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10](=[O:27])[NH:11][C:12]2[CH:25]=[CH:24][C:15]([O:16][CH2:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[CH:14][C:13]=2[CH3:26])=[O:8])=[CH:28][CH:29]=1)(=[S:36])[NH2:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 1049PyridineHCID 23370059HCID 23370059, compound

Product 1

HCID 23370011HCID 23370011, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a similar manner to Example 1, starting material step (b), the product of step (c) (11.36 g), pyridine (500 ml), triethylamine (70 ml) and H2S gas were reacted to give isopropyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]-3-methylphenoxyacetate (12.23 g) as a yellow solid: NMR Spectrum (DMSO-d6) 1.24 (6H, d), 2.28 (3H, s), 4.69 (2H, s), 5.01 (1H, m), 6.78 (1H, dd), 6.85 (1H, d), 7.77 (1H, d), 7.96 (2H, d), 8.05 (2H, d), 9.65 (1H, br s), 10.04 (1H, br s), 10.56 (1H, s), 11.11 (1H, s); Mass Spectrum m/Z 452 (M+Na)+.

Sources & evidence

ORD record
ord-8e64147dac204dbaad923084db3000a1
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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