Pyridine → 2-Acetylamino-3-(o-chlorobenzoyl)-5-ethylthiophene

HRID 1076600Notes

Reaction equation

HRID 1076600 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:16][CH3:17])=[CH:5][C:6]=1[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14].N1C=CC=CC=1.[CH3:24][CH2:25][O:26]CC.C(Cl)(=O)C>O>[C:25]([NH:1][C:2]1[S:3][C:4]([CH2:16][CH3:17])=[CH:5][C:6]=1[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])(=[O:26])[CH3:24]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 13163365(2-Amino-5-ethylthiophen-3-yl)(2-chlorophenyl)methanone

Product 1

HCID 215377752-Acetylamino-3-(o-chlorobenzoyl)-5-ethylthiophene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 46.4 g of 2-amino-3-(o-chlorobenzoyl)-5-ethylthiophene, 46.4 g of pyridine and 1160 ml of anhydrous ether is added dropwise 46.4 g of acetyl chloride. Then the reaction mixture is stirred under reflux for 2 hours. After cooling, the reaction mixture is poured into water. The ether layer is separated and washed with water, and dried over sodium sulfate. The solvent is removed under reduced pressure to give crystals of 2-acetylamino-3-(o-chlorobenzoyl)-5-ethylthiophene, which are recrystallized from ethanol-ether to give crystals having a melting point of 132° - 134°C; yield 42.44 g (79%).

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureAfter cooling
  3. customThe ether layer is separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-f2468bdc9d9749039233ea1e15d1511b
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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