Potassium Hydroxide → HCID 21537722, compound

HRID 1076612Notes

Reaction equation

HRID 1076612 reaction equation
CC[C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([CH3:20])[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>[CH3:3][NH:5][C:6]1[S:7][CH:8]=[C:9]([CH3:20])[C:10]=1[C:11](=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 21537737HCID 21537737, compound

Product 1

HCID 21537722HCID 21537722, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 29.6 g of 2-(N-methylacetylamino)-3-(o-chlorobenzoyl)-4-methylthiophene in 592 ml of ethanol, is added 6.97 g of potassium hydroxide in 190 ml of water. The mixture is heated at 95°C for 1 hour, evaporated under reduced pressure to a residue. Water is added to the residue and extracted with chloroform. The chloroform extracts are washed with water, dried over sodium sulfate, then evaporated under reduced pressure to give an oil. The residual oil is chromatographed on silica gel, using chloroform as an eluent to give 2-methylamino-3-(o-chlorobenzoyl)-4-methylthiophene as crystals having a melting point of 132° - 134°C (after recrystallization from ethanol).

Workup

  1. customevaporated under reduced pressure to a residue
  2. additionWater is added to the residue
  3. extractionextracted with chloroform
  4. washThe chloroform extracts are washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customto give an oil
  8. customThe residual oil is chromatographed on silica gel

Sources & evidence

ORD record
ord-05ba35e44a3a49c69de83505f297de46
Source dataset
uspto-grants-1976_05
Patent number
US03957783

Reaction notes

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