Chloromethyl ethyl ether → HCID 19896213, compound

HRID 1196763Notes

Reaction equation

[H-].[Na+].[F:3][C:4]([F:28])([F:27])[O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[NH:14][C:13]2=[O:26])=[CH:8][CH:7]=1.Cl[CH2:30][O:31][CH2:32][CH3:33]>CN(C)C=O>[CH2:32]([O:31][CH2:30][N:14]1[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])=[CH:16][C:17](=[O:18])[N:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][C:4]([F:3])([F:27])[F:28])=[CH:7][CH:8]=2)[C:13]1=[O:26])[CH3:33]

Participants

Conditions

Temperature: 0 °C

Procedure

0.5 g of sodium hydride (purity: 55%) was added to 50 ml of dimethylformamide, and then 3.8 g of 3-(4-trifluoromethoxyphenyl)-6-(2-chlorophenyl)-2,4(1H,3H)-pyrimidinedione was added to the solution with stirring at 0° C. The resulting solution was stirred at room temperature for 15 minutes, then added dropwise with 1.3 g of chloromethylethyl ether and further stirred at room temperature for 3 hours. The reaction mixture was added into 200 ml of ice water and extracted with 200 ml of ethyl acetate. The organic layer was washed with water and dried, and then the solvent was distilled away under reduced pressure to obtain 3.8 g of a crude product. This crude product was recrystallized from diisopropyl ether to obtain 3.2 g of the objective compound.

Workup

stirringThe resulting solution was stirred at room temperature for 15 minutes
stirringfurther stirred at room temperature for 3 hours
extractionextracted with 200 ml of ethyl acetate
washThe organic layer was washed with water
customdried
distillationthe solvent was distilled away under reduced pressure
customto obtain 3.8 g of a crude product
customThis crude product was recrystallized from diisopropyl ether

Sources & evidence

ORD record: ord-067e833919b646e28bafaac06468cade
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05116404

Reaction notes

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