Ammonia → 4-(Chloromethyl)-2-(4-chlorophenyl)-5-methyl-1,3-oxazole

HRID 1916262Notes

Reaction equation

HRID 1916262 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:15])=[C:11]([CH3:14])[N+:12]=2[O-])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:18])=O.N>C(Cl)(Cl)Cl>[Cl:18][CH2:14][C:11]1[N:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[O:9][C:10]=1[CH3:15]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 32439522-(4-Chlorophenyl)-4,5-dimethyl-1,3-oxazol 3-oxide

Product 1

HCID 36136584-(Chloromethyl)-2-(4-chlorophenyl)-5-methyl-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

1.00 g (4.47 mmol) of the compound from Example 13A were initially charged in 15 ml of chloroform, and 1.5 ml (16.10 mmol) of phosphorus oxychloride were added carefully. With stirring, the reaction mixture was heated under reflux for 30 min. The reaction was then cooled to 0° C. and made slightly basic by addition of 25% strength aqueous ammonia solution. The mixture was extracted three times with in each case 20 ml of ethyl acetate. The combined organic phases were washed twice with in each case 5 ml of water and then dried over magnesium sulfate. The solvent was removed on a rotary evaporator. Without further purification, the residue was used for the subsequent steps.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 30 min
  3. extractionThe mixture was extracted three times with in each case 20 ml of ethyl acetate
  4. washThe combined organic phases were washed twice with in each case 5 ml of water
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed on a rotary evaporator
  7. customWithout further purification

Sources & evidence

ORD record
ord-962d86d60f4146a5b2ed0edd8944f1dd
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

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