Ammonia → HCID 69291056, compound

HRID 2113868Notes

Reaction equation

HRID 2113868 reaction equation
[F:1][C:2]1([F:16])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=[CH:12][C:13](O)=[O:14])=[CH:10][C:4]=2[O:3]1.C(Cl)(=O)C(Cl)=O.[NH3:23]>O1CCCC1.CN(C)C=O>[F:1][C:2]1([F:16])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=[CH:12][C:13]([NH2:23])=[O:14])=[CH:10][C:4]=2[O:3]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 2774070HCID 2774070, compound

Product 1

HCID 69291056HCID 69291056, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

To a suspension of 8.00 g (35.1 mmol) 3-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-acrylic acid in 40 ml tetrahydrofuran and 0.4 ml N,N-dimethyl formamide, 3.86 ml (45.0 mmol) oxalyl chloride 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 34 ml of an 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. 7.20 g (90%) 3-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-acrylamide were obtained.

Workup

  1. additionwas added dropwise at 0° C. within 10 min
  2. customwas collected
  3. washwashed with water
  4. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-3c3f2f3042b247fcb6795e97a159c93c
Source dataset
uspto-grants-2008_10
Patent number
US07432291B2

Reaction notes

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