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

HRID 259697Notes

Reaction equation

HRID 259697 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-7e1b3307ac0846ff897be254a16843b3
Source dataset
uspto-grants-1996_06
Patent number
US05523280

Reaction notes

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