1,3-Dichloroacetone → HCID 68981663, compound

HRID 475554Notes

Reaction equation

HRID 475554 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12]([NH2:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:26][CH2:27][C:28](=O)[CH2:29]Cl>C(O)CC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:12]2[O:13][CH:29]=[C:28]([CH2:27][Cl:26])[N:14]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 404187363,4-Bis(benzyloxy)benzamide

Product 1

HCID 68981663HCID 68981663, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A 37.9 g quantity of 3,4-dibenzyloxybenzamide and 28.8 g of 1,3-dichloro-2-propanone were suspended in 500 ml of propanol, and the suspension was heated and refluxed for 3 days. After cooling, the reaction mixture was concentrated to half its original volume under reduced pressure and 300 ml of diisopropyl ether was added. The precipitated crystals were collected by filtration and recrystallized from acetone-methanol-diisopropyl ether. The obtained crystals were dried under reduced pressure to give 20.1 g of colorless powdery 2-(3,4-bis(benzyloxy)phenyl)-4-chloromethyloxazole.

Workup

  1. temperaturethe suspension was heated
  2. temperaturerefluxed for 3 days
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated to half its original volume under reduced pressure and 300 ml of diisopropyl ether
  5. additionwas added
  6. filtrationThe precipitated crystals were collected by filtration
  7. customrecrystallized from acetone-methanol-diisopropyl ether
  8. customThe obtained crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-459b2b5435984085af6de8be3a9e496d
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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