Triethylamine → HCID 178441582, compound

HRID 2233578Notes

Reaction equation

[CH2:1]([C:5]1[N:6]=[C:7]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]#[N:20])=[C:14]([Cl:21])[CH:13]=1)[CH2:2][CH2:3][CH3:4].Cl.[NH2:33][OH:34].C(N(CC)CC)C>O1CCCC1.CO>[CH2:1]([C:5]1[N:6]=[C:7]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:26][CH:27]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH:33][OH:34])=[NH:20])=[C:14]([Cl:21])[CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

2.2 g {4-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-chloro-phenyl}-acetonitrile were dissolved in a mixture of 6 ml tetrahydrofuran and 12 ml methanol. 3.3 g hydroxylamine hydrochloride were added followed by the addition of 6.6 ml triethylamine. The reaction mixture was stirred at 60° C. for two hours. The solvents were removed in vacuo and the resulting residue poured into water and extracted five times with portions of 30 ml ethylacetate. The combined organic extracts were dried over MgSO4 and the solvent was evaporated in vacuo to provide 2.3 g 2-{4-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-chloro-phenyl}-N-hydroxy-acetamidine as crude material.

Workup

customThe solvents were removed in vacuo
additionthe resulting residue poured into water
extractionextracted five times with portions of 30 ml ethylacetate
dry with materialThe combined organic extracts were dried over MgSO4
customthe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-9f29ec8d1c7747abb1ff1abd2c5d5489
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709509B2

Reaction notes

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