4-Chlorobenzoyl chloride → 4-Chloro-N-[2-(furan-2-yl)-2-oxoethyl]benzamide

HRID 235888Notes

Reaction equation

HRID 235888 reaction equation
Cl.[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([CH2:9][NH2:10])=[O:8].C(=O)(O)[O-].[Na+].C(OCC)(=O)C.[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1>O>[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH:10][CH2:9][C:7]([C:3]2[O:2][CH:6]=[CH:5][CH:4]=2)=[O:8])=[O:28])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 85014-Chlorobenzoyl chlorideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 132261382-Amino-1-(furan-2-yl)ethan-1-one--hydrogen chloride (1/1)

Product 1

HCID 133614284-Chloro-N-[2-(furan-2-yl)-2-oxoethyl]benzamideYield 98.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 10 g of (2-furylcarbonyl)methylamine hydrochloride, 12.5 g of sodium bicarbonate, 200 ml of ethyl acetate and 100 ml of water are dropwise added 12.0 g of 4-chlorobenzoyl chloride at a temperature below 10° C. under stirring. The mixture is stirred at room temperature for 3 hours. Then, the ethyl acetate layer is collected, washed with water and dried. Said ethyl acetate layer is evaporated under reduced pressure to remove solvent. 16.0 g of N-(4-chlorobenzoyl)-(2-furylcabonyl)methylamine are thereby obtained. Yield: 98.2%

Workup

  1. customat a temperature below 10° C.
  2. stirringThe mixture is stirred at room temperature for 3 hours
  3. customThen, the ethyl acetate layer is collected
  4. washwashed with water
  5. customdried
  6. customis evaporated under reduced pressure
  7. customto remove solvent

Sources & evidence

ORD record
ord-4a359727c8094b9190ab91730f2d13e8
Source dataset
uspto-grants-1987_02
Patent number
US04642313

Reaction notes

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