Ammonia → HCID 69112309, compound

HRID 2113865Notes

Reaction equation

HRID 2113865 reaction equation
[F:1][CH:2]([F:15])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12](O)=[O:13])=[CH:6][CH:5]=1.C(Cl)(=O)C(Cl)=O.[NH3:22]>O1CCCC1.CN(C)C=O>[F:1][CH:2]([F:15])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]([NH2:22])=[O:13])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 7039363-(4-Difluoromethoxy-phenyl)-acrylic acid

Product 1

HCID 69112309HCID 69112309, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a suspension of 8.70 g (40.6 mmol) 3-(4-difluoromethoxy-phenyl)-acrylic acid in 60.0 ml tetrahydrofuran and 0.6 ml N,N-dimethylformamide a solution of 5.14 ml (60.9 mmol) oxalyl chloride in 10 ml tetrahydrofuran was added dropwise at 0° C. within 10 min. Stirring was continued at 0-5° C. for 30 min. and 2 h at room temperature thereafter. The resulting solution was cooled to 0-5° C. again and then added within 15 min. to 150 ml of a 25% aqueous ammonia solution. The separating oil was collected and stirred for 30 min. with water. The precipitated amide was collected, washed with water and dried at 40° C. in vacuo. 4.7 g (54%) 3-(4-Difluoromethoxy-phenyl)-acrylamide.

Workup

  1. additionwas added dropwise at 0° C. within 10 min
  2. customThe separating oil was collected
  3. stirringstirred for 30 min. with water
  4. customThe precipitated amide was collected
  5. washwashed with water
  6. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-dc0930d297674c50a4e779a232f7c984
Source dataset
uspto-grants-2008_10
Patent number
US07432291B2

Reaction notes

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