Acetone → HCID 18537009, compound

HRID 2298591Notes

Reaction equation

HRID 2298591 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([S:10][CH3:11])=[C:7]([C:12](=S)[NH2:13])[CH:6]=1)=[O:4].Br[CH2:16][C:17]([C:19]1[CH:20]=[C:21]([C:25](OC)=S)[S:22][C:23]=1C)=O.[CH3:29]C(C)=O>>[CH3:11][S:10][C:8]1[S:9][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][C:7]=1[C:12]1[N:13]=[C:23]([C:19]2[CH:17]=[CH:16][CH:25]=[CH:21][CH:20]=2)[S:22][CH:29]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 18536903HCID 18536903, compoundHCID 86583828Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 18537009HCID 18537009, compoundYield 65%

Procedure

5-(Methoxycarbonyl)-2-(methylthio)-thiophene-3-thiocarboxamide (100 mg, 0.4 mmol, Maybridge Chemical Company, Cornwall, UK) was dissolved in acetone (20 ml). To this solution, methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (112 mg) as prepared in previous step was added and heated at reflux for 3 h. At this point the solid that precipitated was filtered off and washed with acetone and dried under vacuum to give 82 mg (65%) of methyl 5-methylthio-4-(2-phenyl(1,3-thiazol-4-yl))thiophene-2-carboxylate. 1H-NMR (CDCl3; 300 MHz) δ2.67 (s, 3H), 3.91 (s, 3H), 7.44-7.49 (m, 3H), 7.61 (s, 1H), 8.03-8.06 (m, 2H), 8.28 (s, 1H).

Workup

  1. additionwas added
  2. temperatureheated
  3. temperatureat reflux for 3 h
  4. customAt this point the solid that precipitated
  5. filtrationwas filtered off
  6. washwashed with acetone
  7. customdried under vacuum

Sources & evidence

ORD record
ord-790b95e974204d3e96a62d90be99f2d8
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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