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Methylamine → 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-n-hydroxy-2,n'-dimethyl-benzamidine

HRID 471369
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HRID 471369 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([CH:18]=[N:19][OH:20])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl[N:29]1C(=O)CC[C:30]1=O.CN.C(N(CC)CC)C>CN(C=O)C.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:25])([F:27])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:19][OH:20])=[N:29][CH3:30])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1
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HCID 6329MethylamineHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 1363862674-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde oxime2회

생성물 1

HCID 1358900134-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-n-hydroxy-2,n'-dimethyl-benzamidine수율 39%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

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온도
75 °C

실험 절차

To a solution of 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde oxime (i.e. the product of Step 2, 500 mg) in DMF (25 mL) was added N-chloro succinimide (168 mg) and heated to 75° C. for 1 h. After cooling, the reaction mixture was poured onto water and extracted with MTBE. 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 methylamine (0.66 mL, 41 mg) and triethylamine (0.18 mL, 0.13 g) in THF 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 (270 mg, 39%) as a colorless solid.

후처리

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured onto water
  3. extractionextracted with MTBE
  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

출처 및 근거

ORD 기록
ord-de7079c22e0d458b9e79585448c73ea2
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08633134B2

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