Triethylamine → HCID 178432700, compound

HRID 2263419Notes

Reaction equation

HRID 2263419 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[O:16][C:15]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[N:14][C:13]=2[CH3:29])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[NH2:31][OH:32].C(N(CC)CC)C>O1CCCC1.CO>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[O:16][C:15]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:28])[F:27])=[CH:21][CH:20]=3)=[N:14][C:13]=2[CH3:29])[CH:7]=[CH:6][C:3]=1[C:4]([NH:31][OH:32])=[NH:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 59594672HCID 59594672, compound

Product 1

HCID 178432700HCID 178432700, compoundYield 136%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

3.0 g 2-Chloro-4-{4-methyl-2-[2-(4-trifluoromethyl-phenyl)-ethyl]-oxazol-5-ylmethoxy}-benzonitrile were dissolved in a mixture of 20 ml tetrahydrofuran and 20 ml methanol. 9.91 g hydroxylamine hydrochloride were added followed by the addition of 19.9 ml triethylamine. The reaction mixture was stirred at 65° C. overnight. 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 4.4 g crude 2-chloro-N-hydroxy-4-{4-methyl-2-[2-(4-trifluoromethyl-phenyl)-ethyl]-oxazol-5-ylmethoxy}-benzamidine which was used without further purification.

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-1708e11c04174ded8db4f2dc31000cd4
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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