Iodoethane → HCID 19085270, compound

HRID 963068Notes

Reaction equation

HRID 963068 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][C:3]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17].C(=O)([O-])[O-].[K+].[K+].[CH2:25](I)[CH3:26]>CC(C)=O>[NH2:1][C:2]1[S:6][C:5]([C:7]([O:9][CH2:25][CH3:26])=[O:8])=[CH:4][C:3]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 13670763HCID 13670763, compound

Product 1

HCID 19085270HCID 19085270, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Amino-4-(2-chlorobenzoyl)thiophene-2-carboxylic acid (240 g), potassium carbonate (176 g) and ethyl iodide (150 ml) were added to acetone (5 l), and the mixture was refluxed overnight. The solvent was evaporated, and ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution were added. The precipitated layer was taken out, washed with brine, dried over sodium sulfate and concentrated. The resulting crystals were collected by filtration and washed with ethyl acetate to give 126 g of ethyl 5-amino-4-(2-chlorobenzoyl)thiophene-2-carboxylate.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe solvent was evaporated
  3. additionethyl acetate and a saturated aqueous sodium hydrogencarbonate solution were added
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. filtrationThe resulting crystals were collected by filtration
  8. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-fff37e91469d4b229240c56969d78a24
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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