Triethylamine → 4-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-trifluoromethyl-benzamide

HRID 2233582Notes

Reaction equation

HRID 2233582 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=1)[CH2:2][CH2:3][CH3:4].Cl.[NH2:35][OH:36].C(N(CC)CC)C>O1CCCC1.CO>[CH2:1]([C:5]1[N:6]=[C:7]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]([NH:35][OH:36])=[NH:17])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=1)[CH2:2][CH2:3][CH3:4].[CH2:1]([C:5]1[N:6]=[C:7]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]([NH2:17])=[O:36])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 59296163HCID 59296163, compound

Product 2

HCID 866138984-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-trifluoromethyl-benzamideHCID 178441583HCID 178441583, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 180 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-trifluoromethyl-benzonitrile in 5 mL of tetrahydrofuran and 10 ml of methanol was added 267 mg of hydroxylamine hydrochloride followed by 0.55 mL of triethylamine. The resulting mixture was heated to 60° C. overnight. The solvents were removed in vacuo, the resulting residue was poured into water and extracted with ethylacetate. The organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (heptane 1/ethyl acetate 1) to give 90 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-N-hydroxy-2-trifluoromethyl-benzamidine and 50 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-trifluoromethyl-benzamide.

Workup

  1. customThe solvents were removed in vacuo
  2. additionthe resulting residue was poured into water
  3. extractionextracted with ethylacetate
  4. dry with materialThe organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel (heptane 1/ethyl acetate 1)

Sources & evidence

ORD record
ord-722dc581849240309170170d5d7091d6
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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