Ammonia → 3-(3-Trifluoromethoxy-phenyl)-acrylamide

HRID 1271431Notes

Reaction equation

HRID 1271431 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12](O)=[O:13])[CH:7]=[CH:8][CH:9]=1.C(Cl)(=O)C(Cl)=O.[NH3:23]>C1COCC1.CN(C)C=O>[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]([NH2:23])=[O:13])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 735839HCID 735839, compound

Product 1

HCID 694896963-(3-Trifluoromethoxy-phenyl)-acrylamideYield 45%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-(3-trifluoromethoxy-phenyl)-acrylic acid (2.21 g, 9.53 mmol) in THF (15 ml) and N,N-dimethyl formamide (0.2 ml) a solution oxalyl chloride (2.42 g, 19.06 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 0.99 g (45%) 3-(3-trifluoromethoxy-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-fad7de130a1d4940905ed61527860ed2
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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