Dimethylformamide → Methyl-4-[(5-methyl-4-phenyl(1,3-thiazol-2-yl))amino]-5-methylthiothiophene-2-carboxylate

HRID 2298669Notes

Reaction equation

HRID 2298669 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[CH:6]=[C:7]([C:11]([O:13][CH3:14])=[S:12])[S:8][C:9]=1[CH3:10])=[S:3].Br[CH:16](C)[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O.[CH3:26]N(C=O)C>>[CH3:14][O:13][C:11]([C:7]1[S:8][C:9]([CH3:10])=[C:5]([NH:4][C:2]2[S:3][CH:16]=[C:17]([C:19]3[CH:20]=[C:21]([CH3:26])[CH:22]=[CH:23][CH:24]=3)[N:1]=2)[CH:6]=1)=[S:12]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 164522-BromopropiophenoneHCID 86583851Methyl 4-[(aminothioxomethyl)amino]-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86584791Methyl-4-[(5-methyl-4-phenyl(1,3-thiazol-2-yl))amino]-5-methylthiothiophene-2-carboxylateYield 100%

Procedure

Using a procedure similar to Example 204, step (a), 51 mg (0.19 mmol) of methyl 4-[(aminothioxomethyl)amino]-5-methylthiothiophene-2-carboxylate was allowed to react with 41.4 mg (0.38 mmol) of 2-bromopropiophenone (Aldrich Chemical Co., Milwaukee, Wis.) in 2 mL of DMF for 4 h. Concentration in vacuo of the reaction mixture afforded 73 mg (100%) of methyl-4-[(5-methyl-4-phenyl(1,3-thiazol-2-yl))amino]-5-methylthiothiophene-2-carboxylate. Mass spectrum (ESI, m/z): Calcd. for C17H16N2O2S3, 377.05 (M+H), found 377.2.

Workup

  1. concentrationConcentration in vacuo of the reaction mixture

Sources & evidence

ORD record
ord-42a61b56cfe14447b41058717a057958
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

Loading…