Ammonia → HCID 231006, compound

HRID 1271388Notes

Reaction equation

HRID 1271388 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17]([OH:19])=O)=[CH:11][CH:10]=1.[NH3:20]>O1CCCC1.CN(C)C=O>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17]([NH2:20])=[O:19])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 132454-Methoxy cinnamic acidHCID 65578Oxalyl chloride

Product 1

HCID 231006HCID 231006, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

44.5 ml (351 mmol) oxalyl chloride was added dropwise at 0° C. within 45 min. to a suspension of 50.0 g (281 mmol) 3-(4-Methoxyphenyl)-acrylic acid in 300 ml tetrahydrofuran and 3.0 ml N,N-dimethyl formamide. Stirring was continued at 0–5° C. for 30 min. and thereafter for 2 h at room temperature. The resulting solution was cooled to 0–5° C. again and then added within 15 min. to 750 ml of a 25% aqueous solution of ammonia. After stirring for 30 min. the precipitated amide was collected, washed with water and dried at 40° C. in vacuo. 48.8 g (98%) 3-(4-Methoxyphenyl)-acrylamide were obtained.

Workup

  1. waitfor 2 h at room temperature
  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-e9f57b05f838490d9c0041e3d9d5dbfe
Source dataset
uspto-grants-2007_04
Patent number
US07205325B2

Reaction notes

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