Hydrochloric Acid → N4-cyclohexylmethyl-2-fluoro-5-nitro-N1-phenyl-benzene-1,4-diamine

HRID 1241933노트

반응식

HRID 1241933 반응식
[F:1][C:2]1[CH:14]=[C:13](F)[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:19]1([CH2:25][NH2:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.CCN(C(C)C)C(C)C.Cl>CN(C=O)C>[CH:19]1([CH2:25][NH:26][C:13]2[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][C:3]([NH:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[C:2]([F:1])[CH:14]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 76688CyclohexanemethylamineHCID 81531DiisopropylethylamineHCID 219378022,4-difluoro-5-nitro-N-phenylaniline

생성물 1

HCID 21061670N4-cyclohexylmethyl-2-fluoro-5-nitro-N1-phenyl-benzene-1,4-diamine수율 34.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 2,4-difluoro-5-nitro-N-phenylaniline (1.00 g, 4.00 mmol), cyclohexanemethylamine (0.57 mL, 4.40 mmol) and N,N′-diisopropylethylamine (0.77, 4.40 mmol) in DMF (40 mL) was stirred at room temperature under an inert atmosphere for 18.5 h. The reaction mixture was transferred to a separatory funnel containing 2 N HCl. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with water, brine and dried over MgSO4. The solution was filtered through diatomaceous earth and the solvent was evaporated. The resulting dark red residue was flash chromatographed (10% EtOAc/hexanes) to give N4-cyclohexylmethyl-2-fluoro-5-nitro-N1-phenyl-benzene-1,4-diamine as a dark red solid (0.48 g, 34.9% yield). M+, 344

후처리

  1. customThe reaction mixture was transferred to a separatory funnel
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic layers were washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered through diatomaceous earth
  6. customthe solvent was evaporated
  7. customchromatographed (10% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-1ffcbcf32ede4c709e1790ce80c7c84c
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115644B2

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