Triethylamine → 2-Chloro-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-n-hydroxy-n'-(2,2,2-trifluoro-ethyl)-benzamidine

HRID 471384노트

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HRID 471384 반응식
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]2[CH2:15][C:14]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[CH:4]=[N:5][OH:6].ClN1C(=O)CCC1=O.[F:36][C:37]([F:41])([F:40])[CH2:38][NH2:39].C(N(CC)CC)C>CN(C=O)C.C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]([C:11]2[CH2:15][C:14]([C:20]3[CH:21]=[C:22]([Cl:27])[CH:23]=[C:24]([Cl:26])[CH:25]=3)([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH:5][OH:6])=[N:39][CH2:38][C:37]([F:41])([F:40])[F:36]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 31398ChlorosuccinimideHCID 1363862682-Chloro-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzaldehyde Oxime

생성물 1

HCID 1358900292-Chloro-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-n-hydroxy-n'-(2,2,2-trifluoro-ethyl)-benzamidine수율 40%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

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온도
75 °C

실험 절차

To a solution of 2-Chloro-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzaldehyde oxime (i.e. the product of Step 3, 250 mg) in DMF (5 mL) was added N-chloro succinimide (81 mg) and heated to 75° C. for 1 h. After cooling, the reaction mixture was poured onto ice-water and extracted with EtOAc. The combined organic layers were washed with water, dried (Na2SO4) and concentrated in vacuo to ¼ the original volume to obtain the crude hydroxamic acid chloride. This mixture was added to a solution of 2,2,2-trifluoro ethylamine (57 mg) and triethylamine (0.15 mL, 0.11 g) in THF (10 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 (122 mg, 40%).

후처리

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

출처 및 근거

ORD 기록
ord-42b8cee9da5d4172b66a00ff47b04cc9
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633134B2

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