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

HRID 1241933ノート

反応式

HRID 1241933 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-1ffcbcf32ede4c709e1790ce80c7c84c
出典データセット
uspto-grants-2006_10
特許番号
US07115644B2

反応ノート

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