Pyridine → AK-660/12300001

HRID 1076594Notes

Reaction equation

HRID 1076594 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1.[CH3:25][CH2:26][O:27]CC.C(Cl)(=O)C>O>[C:26]([NH:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:27])[CH3:25]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 6861613-Benzoyl-4,5,6,7-tetrahydro-1-benzothiophen-2-amine

Product 1

HCID 902348AK-660/12300001

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 35 g of 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene, 35 g of pyridine and 1950 ml of anhydrous ether is added dropwise 35 g of acetyl chloride. Then the reaction mixture is stirred under reflux for 3 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 an oily residure, which is crystallized from ether to give 2-acetylamino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene having a melting point of 116° - 119°C.

Workup

  1. temperatureunder reflux for 3 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
  7. customto give an oily residure, which
  8. customis crystallized from ether

Sources & evidence

ORD record
ord-047f8a08bdad40f9bac4a83f76942a9b
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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