Water → HCID 13937166, compound

HRID 868526Notes

Reaction equation

[OH-].[K+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[C:11]([N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1)=[CH2:12].[Cl:18][C:19]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:20]=1[CH2:21]Cl.O>CS(C)=O>[Cl:18][C:19]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:20]=1[CH2:21][O:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[C:11]([N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1)=[CH2:12]

Participants

Conditions

Temperature: 55 °C

Procedure

85% Potassium hydroxide powder (36.0 g, 0.545 mole) was suspended in dimethyl sulfoxide (500 g) and stirred at 55° C. for 50 minutes. After cooling to 25° C., 1-[1-(2-hydroxy-5-fluorophenyl)vinyl]-1H-imidazole (90.0 g, 0.441 mole) was added and the mixture was stirred at room temperature for 1 hour. Then, 2,4-dichlorobenzyl chloride (94.5 g, 0.483 mole) was added dropwise over 1 hour and the mixture was stirred for 2 hours. Water (680 ml) was added dropwise over 25 minutes to the reaction mixture with stirring and then stirring was continued for additional 1 hour. The precipitated crystals were filtered off and washed with water (135 ml×5) and n-hexane (135 ml×3). The resulting crude crystals were recrystallized from n-hexane/ethyl acetate to obtain the title compound (109 g, 68.1%), m.p. 118°-120° C.

Workup

temperatureAfter cooling to 25° C.
stirringthe mixture was stirred at room temperature for 1 hour
stirringthe mixture was stirred for 2 hours
stirringwith stirring
stirringstirring
waitwas continued for additional 1 hour
filtrationThe precipitated crystals were filtered off
washwashed with water (135 ml×5) and n-hexane (135 ml×3)
customThe resulting crude crystals were recrystallized from n-hexane/ethyl acetate

Sources & evidence

ORD record: ord-2f175da1bbbe4ee6bd04747500df4b36
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04780471

Reaction notes

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