Triethylamine → HCID 178423541, compound

HRID 471371Notes

Reaction equation

HRID 471371 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([C:11]2[CH2:15][C:14]([C:26]([F:29])([F:28])[F:27])([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[O:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[CH:4]=[N:5][OH:6].ClN1C(=O)CCC1=O.[NH2:38][CH2:39][C:40]([NH:42][CH2:43][C:44]([F:47])([F:46])[F:45])=[O:41].C(N(CC)CC)C>CN(C=O)C.C1COCC1>[OH:6][N:5]=[C:4]([NH:38][CH2:39][C:40]([NH:42][CH2:43][C:44]([F:47])([F:46])[F:45])=[O:41])[C:3]1[CH:7]=[CH:8][C:9]([C:11]2[CH2:15][C:14]([C:26]([F:29])([F:27])[F:28])([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=3)[O:13][N:12]=2)=[CH:10][C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 247051432-Amino-N-(2,2,2-trifluoroethyl)acetamideHCID 1371957342-Methyl-4-[5-trifluoromethyl-5-(3-trifluoromethyl-phenyl)-4,5-dihydro-isoxazol-3-yl]-benzaldehyde oxime

Product 1

HCID 178423541HCID 178423541, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 2-Methyl-4-[5-trifluoromethyl-5-(3-trifluoromethyl-phenyl)-4,5-dihydro-isoxazol-3-yl]-benzaldehyde oxime (250 mg) in DMF (8 mL) was added N-chloro succinimide (84 mg) and heated to 75° C. for 1 h. After cooling, the reaction mixture was poured onto water and extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated in vacuo to ¼ of the original volume to obtain the crude hydroxamic acid chloride. This mixture was added to a solution of 2-amino-N-(2,2,2-trifluoro-ethyl)-acetamide (116 mg) and triethylamine (0.30 mL, 0.21 g) in THF (8 mL) and stirred at room temperature over night. After concentration in vacuo, the mixture was purified by chromatography on silica gel to obtain the title compound (146 mg, 43%).

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured onto water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto obtain the crude hydroxamic acid chloride
  7. concentrationAfter concentration in vacuo
  8. customthe mixture was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a6e347dba44d4beabc58fc6a6665a1f4
Source dataset
uspto-grants-2014_01
Patent number
US08633134B2

Reaction notes

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