Triethylamine → HCID 178432506, compound

HRID 2233571Notes

Reaction equation

HRID 2233571 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[S:16][C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[N:14][C:13]=2[CH3:27])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[NH2:29][OH:30].C(N(CC)CC)C>O1CCCC1.CO>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[S:16][C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:26])[F:25])=[CH:19][CH:18]=3)=[N:14][C:13]=2[CH3:27])[CH:7]=[CH:6][C:3]=1[C:4]([NH:29][OH:30])=[NH:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 59296174HCID 59296174, compound

Product 1

HCID 178432506HCID 178432506, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

153 mg of 2-Fluoro-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-ylmethoxy]-benzonitrile were dissolved in a mixture of 1 ml tetrahydrofuran and 2 ml methanol. 265 mg hydroxylamine hydrochloride was added followed by the addition of 0.5 ml triethylamine. The reaction mixture was stirred at 60° C. for twenty hours. The solvents were removed in vacuo and the resulting residue poured into water and extracted five times with ethylacetate. The combined organic extracts were washed with brine, dried over MgSO4 and the solvent was evaporated in vacuo to obtain 138 mg of 2-Fluoro-N-hydroxy-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-ylmethoxy]-benzamidine as crude material.

Workup

  1. customThe solvents were removed in vacuo
  2. additionthe resulting residue poured into water
  3. extractionextracted five times with ethylacetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-81af6fb1cae94cf9af2794a1583a44da
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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