Benzamide → 4-(Chloromethyl)-2-phenyl-1,3-oxazole

HRID 2117231Notes

Reaction equation

HRID 2117231 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][CH2:11][C:12]([CH2:14]Cl)=O>C(OCC)(=O)C>[Cl:10][CH2:11][C:12]1[N:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:8][CH:14]=1

Participants

4

Reactant 2

HCID 2331BenzamideHCID 107931,3-Dichloroacetone

Product 1

HCID 35511964-(Chloromethyl)-2-phenyl-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

Benzamide (1.21 g, 10 mmol) is mixed with 1,3-dichloroacetone (1.26 g, 10 mmol) and the mixture heated to 130° C. and stirred at this temperature for 1 h. The resulting mixture is then cooled, diluted with ethyl acetate, washed with K2CO3 solution (sat.), then brine, dried over MgSO4 and concentrated to give the title compound as a solid, which is used without further purification. MS (ESI) 194 (M+H, Cl pattern)+.

Workup

  1. temperatureThe resulting mixture is then cooled
  2. washwashed with K2CO3 solution (sat.)
  3. dry with materialbrine, dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9f07d6705bb646659a957437e27a12a6
Source dataset
uspto-grants-2008_10
Patent number
USRE040558E1

Reaction notes

Loading…