Potassium Carbonate → HCID 873872, compound

HRID 253018Notes

Reaction equation

HRID 253018 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH2:10])=[O:4].C(=O)([O-])[O-].[K+].[K+].[C:17](Cl)(=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1>C(#N)C.O>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)=[O:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 74374m-Anisoyl chlorideHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 873872HCID 873872, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl-3-amino-2-thiophenecarboxylate (8.00 g, 50.9 mmol) in acetonitrile (100 mL) was added potassium carbonate (1.1 eq., 56.0 mmol, 7.73 g) followed by m-anisoyl chloride (1.05 eq., 53.4 mmol, 7.51 mL) and the mixture heated under reflux for 1 hour. A white precipitate forms. The mixture was cooled in ice-water, diluted with water (100 mL) and the white solid collected by filtration and dried to yield compound 1 (12.78 g). Upon standing, an additional quantity of product precipitated from the water-acetonitrile solution; this was collected in the same fashion. (Total yield: 14.08 g, 95%).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 1 hour
  3. filtrationthe white solid collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-9725902e3d214d3c91db39e431de6c25
Source dataset
uspto-grants-2011_01
Patent number
US07872003B2

Reaction notes

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