Sulfuric Acid → 4-(Chloromethyl)-2-(4-chlorophenyl)-1,3-oxazole

HRID 1916260Notes

Reaction equation

HRID 1916260 reaction equation
Cl[CH2:2][C:3]([CH2:5][Cl:6])=O.[Cl:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=1.S(=O)(=O)(O)O>>[Cl:6][CH2:5][C:3]1[N:14]=[C:12]([C:11]2[CH:15]=[CH:16][C:8]([Cl:7])=[CH:9][CH:10]=2)[O:13][CH:2]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 107931,3-DichloroacetoneHCID 120844-Chlorobenzamide

Product 1

HCID 71315274-(Chloromethyl)-2-(4-chlorophenyl)-1,3-oxazole

Conditions

Temperature
135 °C

Procedure

408 mg (3.21 mmol) of 1,3-dichloroacetone and 500 mg (3.21 mmol) of 4-chlorobenzamide were combined and stirred at 135° C. for 1 h. The mixture was then cooled to RT, 1.1 ml of conc. sulfuric acid were added carefully and the mixture was stirred for another 5 min. Carefully, the mixture was poured onto ice. The precipitate was filtered off and washed with water. After drying, the crude product was used without further purification for the subsequent reaction.

Workup

  1. temperatureThe mixture was then cooled to RT
  2. stirringthe mixture was stirred for another 5 min
  3. additionCarefully, the mixture was poured onto ice
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. customAfter drying
  7. customthe crude product was used without further purification for the subsequent reaction

Sources & evidence

ORD record
ord-74d6f3bff52449d39c1438a469bb3502
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

Loading…