Phenacyl bromide → HCID 18537313, compound

HRID 2298624Notes

Reaction equation

HRID 2298624 reaction equation
[NH2:1][C:2](=[S:14])[C:3]1[CH:4]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[S:6][C:7]=1[O:8][CH3:9].Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O>>[CH3:9][O:8][C:7]1[S:6][C:5]([C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:3]=1[C:2]1[S:14][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:1]=1

Participants

3

Reactant 2

HCID 6259Phenacyl bromideHCID 18536930HCID 18536930, compound

Product 1

HCID 18537313HCID 18537313, compoundYield 10%

Procedure

A solution of 400 mg (1.73 mmol) of methyl 4-(aminothioxomethyl)-5-methoxythiophene-2-carboxylate was reacted with 345 mg (1.73 mmol) of 2-bromoacetophenone (Aldrich, Milwaukee, Wis., USA) in a manner similar to Example 8, step (a) to give methyl 5-methoxy-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxylate (56 mg, 10%) as a solid. 1H-NMR (DMSO-d6; 300 MHz) δ8.22 (s, 1H), 8.14 (s, 1H), 8.05 (m, 2H), 7.47 (m, 2H), 7.36 (m, 1H), 4.26 (s, 3H), 3.85 (s, 3H).

Sources & evidence

ORD record
ord-a9391f47d0a045c590417a892e932808
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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