Hydrogen Sulfide → 2-(4-(4-Morpholinyl)sulfonylphenyl)-thiazole-4-carboxylic acid

HRID 460179Notes

Reaction equation

[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14]([C:16]([OH:18])=[O:17])[N:15]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[O:19]1[CH2:24][CH2:23]N(S(C2C=CC(C#N)=CC=2)(=O)=O)[CH2:21][CH2:20]1.S.BrCC(=O)C(OCC)=O>>[N:1]1([S:2]([C:5]2[CH:6]=[CH:7][C:8]([C:11]3[S:12][CH:13]=[C:14]([C:16]([OH:18])=[O:17])[N:15]=3)=[CH:9][CH:10]=2)(=[O:3])=[O:4])[CH2:23][CH2:24][O:19][CH2:20][CH2:21]1

Participants

Reactant 4

HCID 402Hydrogen Sulfide

HCID 66144Ethyl bromopyruvate

HCID 41328234-(Morpholine-4-sulfonyl)benzonitrile

HCID 187720852-(p-Sulfamoylphenyl)thiazole-4-carboxylic acid

Product 1

HCID 187717392-(4-(4-Morpholinyl)sulfonylphenyl)-thiazole-4-carboxylic acid

Procedure

In a manner similar to that described for the preparation of 2-(4-aminosulfonylphenyl)thiazole-4-carboxylic acid, 460 mg of 4-(morpholinosulfonyl)-benzonitrile was treated with H2S, ethyl bromopyruvate, and LIOH successively to give the title compound. MS m/z: 355 (M+H).

Sources & evidence

ORD record: ord-15c958d961e34d7293d324b2a7288243
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196104B2

Reaction notes

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