Propanamide, N,N-dimethyl- → 1-(2,2-Difluoro-1,3-benzodioxol-4-yl)propanone

HRID 1376320Notes

Reaction equation

HRID 1376320 reaction equation
CN(C)[C:3](=[O:6])[CH2:4]C.[F:8][C:9]1([F:18])[O:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[O:10]1.[CH3:19]OC(OC)N(C)C>>[F:18][C:9]1([F:8])[O:10][C:11]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:19][C:3](=[O:6])[CH3:4])[C:12]=2[O:13]1

Participants

4

Reactant 3

HCID 12965Propanamide, N,N-dimethyl-HCID 741032,2-Difluoro-1,3-benzodioxoleHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 229164921-(2,2-Difluoro-1,3-benzodioxol-4-yl)propanone

Conditions

Temperature
70 °C

Procedure

12 g of 1-(2,2-difluoro-1,3-benzodioxol-4-yl)propanone are prepared by condensation-of N,N-dimethylpropionamide with the lithiated anion of 2,2-difluoro-1,3-benzodioxole obtained according to the procedure described in patent EP 333658, are then dissolved in 14.6 ml (0.11 mol) of N,N-dimethylformamide dimethyl acetal and heated at 70° C. according to the procedure described in Example No. 1. 25 g (0.05 mol) of enaminone thus obtained are dissolved in 130 ml of acetic acid and then 3.3 ml (0.069 mol) of hydrazine hydrate are added. The crude product obtained is purified by trituration in pentane.

Workup

  1. customobtained

Sources & evidence

ORD record
ord-16a5dc7e4c0e43639dba07e459f81a7b
Source dataset
uspto-grants-1997_09
Patent number
US05663119

Reaction notes

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