Ammonia → 3-(4-Fluoro-2-trifluoromethyl-phenyl)-acrylamide

HRID 1271428Notes

Reaction equation

HRID 1271428 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](O)=[O:11])=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH3:23]>C1COCC1.CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([NH2:23])=[O:11])=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 27375833-[4-fluoro-2-(trifluoromethyl)phenyl]prop-2-enoic Acid

Product 1

HCID 694870153-(4-Fluoro-2-trifluoromethyl-phenyl)-acrylamideYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-(4-fluoro-2-trifluoromethyl-phenyl)-acrylic acid (1.22 g, 5.2 mmol) in THF (10 ml) and N,N-dimethyl formamide (0.2 ml) a solution oxalyl chloride (0.99 g, 7.80 mmol) was added dropwise at 0° C. within 45 min. Stirring was continued at 0–5° C. for 30 min. and 3 h at room temperature thereafter. The resulting solution was cooled to 0–5° C. again and then added within 15 min. to 12 ml of a 25% aqueous ammonia solution. After stirring for 30 min. the precipitated amide was collected, washed with water and dried at 40° C. in vacuo yielding 0.53 g (40%) 3-(4-fluoro-2-trifluoromethyl-phenyl)-acrylamide.

Workup

  1. additionwas added dropwise at 0° C. within 45 min
  2. temperatureThe resulting solution was cooled to 0–5° C. again
  3. customwas collected
  4. washwashed with water
  5. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-9aa49c01bb364ecd859b4447699fa3d8
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

Loading…