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

HRID 1873583Notes

Reaction equation

HRID 1873583 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 are combined and stirred at 135° C. for 1 h. The mixture is then cooled to RT, 1.1 ml of conc. sulfuric acid are added carefully and the mixture is stirred for 5 min. The mixture is carefully poured onto ice. The precipitate is filtered off with suction and washed with water. After drying the crude product is used in the next reaction without further purification.

Workup

  1. temperatureThe mixture is then cooled to RT
  2. stirringthe mixture is stirred for 5 min
  3. additionThe mixture is carefully poured onto ice
  4. filtrationThe precipitate is filtered off with suction
  5. washwashed with water
  6. dry with materialAfter drying the crude product
  7. customis used in the next reaction without further purification

Sources & evidence

ORD record
ord-e48678b65c9a40edabf8327d0057f426
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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