Ammonium Chloride → (3-ethylphenyl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methanol

HRID 2105053Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[N:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:3]1.[Li]CCCC.[CH2:18]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=[O:24])[CH3:19].[Cl-].[NH4+]>C1COCC1>[CH2:18]([C:20]1[CH:21]=[C:22]([CH:23]([C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:5]=2)[OH:24])[CH:25]=[CH:26][CH:27]=1)[CH3:19]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 1-methyl-3-phenyl-1H-1,2,4-triazole (284 mg, 1.8 mmol, see J. Chem. Soc., 1954, 3319-3322) in THF (112 mL) at −78° C. was added BuLi (1.15 mL, 1.6 M in hexanes, 1.8 mmol). The reaction was stirred for 5 minutes at -78° C. and a solution of intermediate 370.1 (200 mg, 1.5 mmol) in THF (2 mL) was added dropwise. The mixture was warmed to ambient temperature over 2 h. Ammonium chloride (80 mg) was added to the mixture and it was concentrated. Purification of the crude material afforded 350 mg of intermediate 370.2 as a white solid. LCMS 294.2 (M+H)+.

Workup

temperatureThe mixture was warmed to ambient temperature over 2 h
concentrationwas concentrated
customPurification of the crude material

Sources & evidence

ORD record: ord-5c8093b6e5674cf79276a67fecbf85d8
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576098B2

Reaction notes

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