Ammonia → 4-(Chloromethyl)-2-(4-chlorophenyl)-5-ethyl-1,3-oxazole
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
Conditions
- Temperature
- 0 °C
Procedure
1.00 g (4.21 mmol) of the compound from example 36A is dissolved in 15 ml of chloroform, and 1.4 ml (15.15 mmol) of phosphoryl chloride is added carefully. The mixture is heated at reflux and stirred at this temperature for 30 min. The mixture is then cooled to 0° C. and made weakly basic using aqueous ammonia. The reaction mixture is extracted three times with in each case 20 ml of ethyl acetate. The combined organic phases are washed once with 10 ml of water and then dried over magnesium sulphate. The solvent is removed on a rotary evaporator, and the residue is dried under reduced pressure in a drying cabinet. Without further purification, the product obtained in this manner is used for the subsequent reactions.
Workup
- temperatureThe mixture is heated
- temperatureat reflux
- extractionThe reaction mixture is extracted three times with in each case 20 ml of ethyl acetate
- washThe combined organic phases are washed once with 10 ml of water
- dry with materialdried over magnesium sulphate
- customThe solvent is removed on a rotary evaporator
- customthe residue is dried under reduced pressure in a drying cabinet
- customWithout further purification
- customthe product obtained in this manner
Sources & evidence
- ORD record
- ord-81a89afe76e346f2ac1200d3bfb8922e
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653109B2
Reaction notes
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