1,1-Dichloroacetone → HCID 69428593, compound

HRID 1271389Notes

Reaction equation

HRID 1271389 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1.[Cl:14][CH:15](Cl)[C:16](=O)[CH3:17]>C1(C)C=CC=CC=1>[Cl:14][CH2:15][C:16]1[N:13]=[C:11]([CH:10]=[CH:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[O:12][CH:17]=1

Participants

4

Reactant 2

HCID 105671,1-DichloroacetoneHCID 231006HCID 231006, compound

Product 1

HCID 69428593HCID 69428593, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

MS: M=178.2 (API+). 1H-NMR(400 MHz, D6-DMSO): δ=3.79(s, 1H, OCH3), 6.46(d, 1H, 2-H), 6.97(d, 2H, 3′-/5′-H), 6.99(br, 1H, NH), 7.36(d, 1H, 3-H), 7.44(br, 1H, NH), 7.50(d, 2H, 2′-/6′-H). 48.0 g (271 mmol) 3-(4-Methoxyphenyl)-acrylamide, 44.4 g (350 mmol) dichloro acetone and 400 ml toluene were kept at reflux temperature for 24 h with continuous removal of water by applying a Dean-Stark trap. After removal of solvents in vacuo, the residue was intensively shaken with 600 ml water, the precipitate isolated by filtration, washed with water and heptane. Drying at 40° C. in vacuo gave 56.9 g (84%) 4-Chloromethyl-2-[2-(4-methoxyphenyl)-vinyl]-oxazole.

Workup

  1. temperatureat reflux temperature for 24 h
  2. customwith continuous removal of water
  3. customAfter removal of solvents in vacuo
  4. customthe precipitate isolated by filtration
  5. washwashed with water and heptane
  6. customDrying at 40° C. in vacuo

Sources & evidence

ORD record
ord-0aa3fa12c2d3432787a8688a962f36de
Source dataset
uspto-grants-2007_04
Patent number
US07205325B2

Reaction notes

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