Pyridine → HCID 21537730, compound

HRID 1076610Notes

Reaction equation

HRID 1076610 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:16])[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.[CH3:23][CH2:24][O:25]CC.C(Cl)(=O)C>O>[C:24]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH3:16])[C:6]=1[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])(=[O:25])[CH3:23]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 21537733HCID 21537733, compound

Product 1

HCID 21537730HCID 21537730, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 62 g of 2-amino-(o-chlorobenzoyl)-4-methylthiophene, 62 g of pyridine and 2170 ml of anhydrous ether is added dropwise 62 g of acetyl chloride. The the reaction mixture is stirred under reflux for 4 hours and 30 minutes. 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 an oily residure, which is crystallized from ethanol to give 2-acetylamino-3-(o-chlorobenzoyl)-4-methylthiophene having a melting point of 148° - 149°C.

Workup

  1. temperatureunder reflux for 4 hours and 30 minutes
  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
  7. customto give an oily residure, which
  8. customis crystallized from ethanol

Sources & evidence

ORD record
ord-8ef1deacefc141beb3e639c237dfc962
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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