Water → HCID 11749519, compound

HRID 1386118Notes

Reaction equation

C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[C:14]1[N:18]=[C:17]([C:19]2[S:20][C:21](Br)=[C:22]([Br:25])[C:23]=2[CH3:24])[N:16]([CH3:27])[N:15]=1.O>C1COCC1>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[C:14]1[N:18]=[C:17]([C:19]2[S:20][CH:21]=[C:22]([Br:25])[C:23]=2[CH3:24])[N:16]([CH3:27])[N:15]=1

Participants

Conditions

Temperature: 25 °C

Procedure

n-Butyl lithium (6.04 mL, 2.5 mmol) was slowly added over a 15 min period to 3-(2-chloro-6-fluorophenyl)-5-(3-methyl-4,5-dibromothien-2-yl) 1-methyl [1,2,4] triazole (7.0 g) in THF (100 mL) at −70° C. under a nitrogen atmosphere and stirred for 1.0 h. After the addition of the distilled water, the reaction was allowed to warm to 25° C. The reaction mixture was extracted with diethyl ether (3×100 mL). The combined ether extracts was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated to crude solid. This was chromatographed on silica gel (EtOAc/Hexane, 1:1) to give 5.0 g (86% yield) 3-(2-chloro-6-fluorophenyl)-5-(3-methyl-4-bromothien-2-yl) 1-methyl [1,2,4] triazole as white solid. MP 111-112° C. ; Anal. Calcd. For C14H10BrClFN3S: C, 43.49; H, 2.61; N, 10.87; S, 8.29. Found; C, 43.79; H, 2.66; N, 10.95; S, 8.28.

Workup

extractionThe reaction mixture was extracted with diethyl ether (3×100 mL)
washThe combined ether extracts was washed with water
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated to crude solid
customThis was chromatographed on silica gel (EtOAc/Hexane, 1:1)

Sources & evidence

ORD record: ord-5694270e43634355baea09edfb8e1201
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265424B1

Reaction notes

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