Ammonia → HCID 3543849, compound

HRID 1271417Notes

Reaction equation

HRID 1271417 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[CH:11][C:12]([OH:14])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.C[N:16](C)C=O.N>O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[CH:11][C:12]([NH2:16])=[O:14])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 169173-(1,3-Benzodioxol-5-yl)prop-2-enoic acid

Product 1

HCID 3543849HCID 3543849, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 50.0 g (260 mmol) 3-Benzo[1,3]dioxol-5-yl-acrylic acid in 300 ml tetrahydrofurane and 3.0 ml N,N-dimethyl formamide 44.5 ml (350 mmol) oxalyl chloride was added dropwise at 0° C. within 45 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 750 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. 49.5 g (99%) 3-Benzo[1,3]dioxol-5-yl-acrylamide were obtained.

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-0e4b48e7b6ee44439f7ad3573d25fb2f
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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