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

HRID 508161Notes

Reaction equation

HRID 508161 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH2:15][CH3:16])=[C:11]([CH3:14])[N+:12]=2[O-])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:19])=O.N>C(Cl)(Cl)Cl>[Cl:19][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[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 582843032-(4-Chlorophenyl)-5-ethyl-4-methyl-1,3-oxazole 3-oxide

Product 1

HCID 582843734-(Chloromethyl)-2-(4-chlorophenyl)-5-ethyl-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

1.00 g (4.21 mmol) of the compound from Example 29A are dissolved in 15 ml of chloroform, and 1.4 ml (15.15 mmol) of phosphoryl chloride are added carefully. The mixture is heated to reflux and stirred at this temperature for 30 min. The mixture is then cooled to 0° C. and made slightly basic using ammonia. The reaction mixture is extracted three times with in each case 20 ml of ethyl acetate. The solvent is removed on a rotary evaporator and the residue is dried in a vacuum drying cabinet. The product is used without further purification in the subsequent reactions.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. extractionThe reaction mixture is extracted three times with in each case 20 ml of ethyl acetate
  4. customThe solvent is removed on a rotary evaporator
  5. customthe residue is dried in a vacuum
  6. customdrying cabinet
  7. customThe product is used without further purification in the subsequent reactions

Sources & evidence

ORD record
ord-206771c8f13e40dd8874837b02bbecb1
Source dataset
uspto-grants-2015_08
Patent number
US09095582B2

Reaction notes

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