1,3-Dichloroacetone → HCID 69292417, compound

HRID 2113869Notes

Reaction equation

HRID 2113869 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]([NH2:15])=[O:14])=[CH:10][C:4]=2[O:3]1.[Cl:17][CH2:18][C:19]([CH2:21]Cl)=O>C1(C)C=CC=CC=1>[Cl:17][CH2:18][C:19]1[N:15]=[C:13]([CH:12]=[CH:11][C:9]2[CH:8]=[CH:7][C:5]3[O:6][C:2]([F:1])([F:16])[O:3][C:4]=3[CH:10]=2)[O:14][CH:21]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 69291056HCID 69291056, compound

Product 1

HCID 69292417HCID 69292417, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.90 g (30.4 mmol) 3-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-acrylamide, 4.76 g (37.5 mmol) 1,3-dichloroacetone and 50 ml toluene were kept at reflux temperature for 48 h with continuous removal of water by applying a Dean-Stark trap. After removal of solvents in vacuo, the residue was treated with 60 ml of a 1:1 mixture of water/isopropanol. After filtration the precipitate was washed first with isopropanol, then with heptane. Drying at 40° C. in vacuo gave 4-Chloromethyl-2-[2-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-vinyl]-oxazole.

Workup

  1. temperatureat reflux temperature for 48 h
  2. customwith continuous removal of water
  3. customAfter removal of solvents in vacuo
  4. additionthe residue was treated with 60 ml of a 1:1 mixture of water/isopropanol
  5. filtrationAfter filtration the precipitate
  6. washwas washed first with isopropanol
  7. customDrying at 40° C. in vacuo

Sources & evidence

ORD record
ord-bb5a744eb9784741abd429926d38b2b4
Source dataset
uspto-grants-2008_10
Patent number
US07432291B2

Reaction notes

Loading…