2-Fluorobenzoyl chloride → 2-(2-Fluorobenzamido)thiophene-3-carboxamide

HRID 1354292

Reaction equation

HRID 1354292 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].[F:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14]>N1C=CC=CC=1>[F:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([NH:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8])=[O:14]

Participants

4

Reactant 2

HCID 98082-Fluorobenzoyl chlorideHCID 6994952-Aminothiophene-3-carboxamide

Product 1

HCID 71641022-(2-Fluorobenzamido)thiophene-3-carboxamideYield 77%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-thiophene-3-carboxylic acid amide (8.73 g, 61.4 mmole) was dissolved in pyridine (100 ml) cooled to 0° C. and 2-fluorobenzoyl chloride was added dropwise over 20 min, then reaction was allowed to warm to room temperature with stirring overnight. The pyridine was removed under vacuum, added dichloromethane and water. Product precipitated as a grey solid and was washed with dilute hydrochloric acid, water and air dried. The dichloromethane layer was separated, washed with dilute hydrochloric acid, and water, dried over sodium sulfate (anh.) and solvent removed to give a total of 12.45 g product (77% yield).

Workup

  1. customreaction
  2. temperatureto warm to room temperature
  3. customThe pyridine was removed under vacuum
  4. additionadded dichloromethane and water
  5. customProduct precipitated as a grey solid
  6. washwas washed with dilute hydrochloric acid, water and air
  7. customdried
  8. customThe dichloromethane layer was separated
  9. washwashed with dilute hydrochloric acid, and water
  10. dry with materialdried over sodium sulfate (anh.) and solvent
  11. customremoved

Sources & evidence

ORD record
ord-018cf2bbc8634588bd8f6562918669b5
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Linked notes

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