Hydrochloric Acid → 4-Phenyl-2-propionylaminothiophene-3-carboxylic amide

HRID 910182Notes

Reaction equation

HRID 910182 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]=1[C:7]([NH2:9])=[O:8].[C:16](Cl)(=[O:19])[CH2:17][CH3:18].C[O-].[Na+].Cl>O.C(O)C.N1C=CC=CC=1>[C:10]1([C:5]2[C:6]([C:7]([NH2:9])=[O:8])=[C:2]([NH:1][C:16](=[O:19])[CH2:17][CH3:18])[S:3][CH:4]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 62324Propionyl chlorideHCID 10942334Sodium MethoxideHCID 167809442-Amino-4-phenylthiophene-3-carboxamide

Product 1

HCID 673819684-Phenyl-2-propionylaminothiophene-3-carboxylic amide

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 2-amino-4-phenylthiophene-3-carboxylic acid amide (3.0 g, 13.8 mmol) and anhydrous pyridine (12 ml) was treated with propionyl chloride (1.32 ml, 15.2 mmol) and stirred at ambient temperature for 3 hours. The excess pyridine was removed in vacuo to give a residue, which was treated with ethanol (50 ml) and sodium methoxide (2.24 g, 41.4 mmol) and the resultant mixture was heated under reflux for 18 hours. The cooled mixture was then diluted with water (300 ml) and acidified with concentrated hydrochloric acid. The resulting solid was collected by filtration, washed with water and dried in vacuo to give 4-phenyl-2-propionylaminothiophene-3-carboxylic amide.

Workup

  1. customThe excess pyridine was removed in vacuo
  2. customto give a residue, which
  3. temperatureunder reflux for 18 hours
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-c8822414241d49c6a992efdefe9c230c
Source dataset
uspto-grants-2011_09
Patent number
US08022076B2

Reaction notes

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