Water → N-(4-fluorobenzoyl)-N-[(3-thienylcarbonyl)methyl]amine

HRID 1462416Notes

Reaction equation

HRID 1462416 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[S:12]1[CH:16]=[CH:15][C:14]([C:17]([CH2:19][NH2:20])=[O:18])=[CH:13]1.C(=O)(O)[O-].[Na+].O>C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:20][CH2:19][C:17]([C:14]2[CH:15]=[CH:16][S:12][CH:13]=2)=[O:18])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 678794-Fluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 131054172-Amino-1-(3-thienyl)ethanone hydrochloride

Product 1

HCID 13105418N-(4-fluorobenzoyl)-N-[(3-thienylcarbonyl)methyl]amineYield 25.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

16 g of 4-fluorobenzoyl chloride are dissolved in 50 ml of ethyl acetate, and the solution is added at a temperature below 10° C. under stirring to a mixture of 17.8 g of N-[(3-thienylcarbonyl)methyl]amine hydrochloride, 25 g of sodium bicarbonate, 100 ml of ethyl acetate and 200 ml of water. The mixture is further stirred at room temperature for 3 hours. The precipitated crystalls are collected by filtration, washed with water and then dried, whereby N-(4-fluorobenzoyl)-N-[(3-thienylcarbonyl)methyl]amine is obtained. On the other hand, the filtrate is washed with water, dried and then condensed under reduced pressure to remove solvent. The residue is washed with ether, whereby N-(4-fluorobenzoyl)-N-[(3-thienylcarbonyl)methyl]amine is further obtained.

Workup

  1. additionthe solution is added at a temperature below 10° C.
  2. filtrationThe precipitated crystalls are collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-f910a9fbb8764ff78919daff0a1e5f13
Source dataset
uspto-grants-1984_07
Patent number
US04460596

Reaction notes

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