Hydrogen Sulfide → HCID 23370042, compound

HRID 1900881Notes

Reaction equation

HRID 1900881 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]([NH:11][C:12](=[O:29])[NH:13][C:14]2[CH:28]=[CH:27][C:17]([O:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:16][CH:15]=2)=[O:10])=[CH:5][CH:4]=1)#[N:2].N1C=CC=CC=1.[SH2:36]>C(N(CC)CC)C>[C:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]([NH:11][C:12](=[O:29])[NH:13][C:14]2[CH:28]=[CH:27][C:17]([O:18][CH2:19][C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])=[CH:16][CH:15]=2)=[O:10])=[CH:5][CH:4]=1)(=[S:36])[NH2:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 1049PyridineHCID 23369993t-Butyl 4-[3-(6-cyanopyrid-3-ylcarbonyl)ureido]phenoxyacetate

Product 1

HCID 23370042HCID 23370042, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a similar manner to Example 1, starting material step (b), the product of step (a) (2.29 g), pyridine (105 ml), triethylamine (15 ml) and H2S gas were reacted to give t-butyl 4-[3-(6-thiocarbamoylpyrid-3-ylcarbonyl)ureido]phenoxyacetate (2.76 g) as a yellow solid: m.p. 248°-249° C. (decomposes); NMR Spectrum (DMSO-d6) 1.44 (9H, s), 4.62 (2H, s), 6.90 (2H, d), 7.49 (2H, d), 8.48 (1H, dd), 8.58 (1H, d), 9.10 (1H, d), 10.02 (1H, bs), 10.30 (1H, br s), 10.49 (1H, s), 11.30 (1H, s); Mass Spectrum m/Z 431 (M+H)+.

Sources & evidence

ORD record
ord-78c4191137f14db8b43a69f890355783
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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