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

HRID 1010822

Reaction equation

HRID 1010822 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 the reaction was allowed to warm to room temperature with stirring overnight. The pyridine was removed under vacuum, dichloromethane and water were added. The product was precipitated as a grey solid and was washed with diluted hydrochloric acid, water and air dried. The dichloromethane layer was separated, washed with diluted hydrochloric acid, and water, dried over sodium sulfate (anh.) and the solvent was removed to give a total of 12.45 g product (77% yield).

Workup

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

Sources & evidence

ORD record
ord-863d6cffb27e476494e14d237ff3589b
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Linked notes

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