Potassium Hydroxide → HCID 13229177, compound

HRID 1076601Notes

Reaction equation

HRID 1076601 reaction equation
CC[C:3]([NH:5][C:6]1[S:7][C:8]([CH2:20][CH3:21])=[CH:9][C:10]=1[C:11](=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=O.[OH-].[K+]>C(O)C.O.C(Cl)(Cl)Cl>[CH3:3][NH:5][C:6]1[S:7][C:8]([CH2:20][CH3:21])=[CH:9][C:10]=1[C:11](=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 21537766HCID 21537766, compound

Product 1

HCID 13229177HCID 13229177, compoundYield 67.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 26.0 g of 2-(N-methylacetylamino)-3-(o-chlorobenzoyl)-5-ethylthiophene in 520 ml of ethanol, is added 5.85 g of potassium hydroxide in 164 ml of water. The mixture is heated at 95°C for 1 hour, then evaporated under reduced pressure to a residue. Water is added to the residue and extracted with dichloromethane. The dichloromethane extracts are washed with water, dried over sodium sulfate, then evaporated under reduced pressure to give crystals, which are chloromatographed on silica gel using chloroform as an eluent to give 15.26 g of 2-(N-methylamino)-3-(o-chlorobenzoyl)-5-ethylthiophene as crystals having a melting point of 100° - 102°C (after recrystallization from ether); yield 67.5%.

Workup

  1. customevaporated under reduced pressure to a residue
  2. additionWater is added to the residue
  3. extractionextracted with dichloromethane
  4. washThe dichloromethane extracts are washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customto give crystals, which

Sources & evidence

ORD record
ord-45a1dfd6e303498c982e770d4672e673
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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