Triethylamine → 4-chloro-N-{3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-2-nitrobenzamide

HRID 1181361ノート

反応式

HRID 1181361 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[NH2:6].C(N(CC)CC)C.[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[C:28]([N+:35]([O-:37])=[O:36])[CH:27]=1>C(Cl)Cl>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:6][C:5]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:31])=[C:28]([N+:35]([O-:37])=[O:36])[CH:27]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 108677844-Chloro-2-nitrobenzoyl chlorideHCID 117365033-Methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)aniline

生成物 1

HCID 589808694-chloro-N-{3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-2-nitrobenzamide収率 69%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]aniline (43 mmol, 10.0 g) in DCM was added triethylamine (52 mmol, 5.2 g) and 4-chloro-2-nitrobenzoyl chloride (9.5 g, 43 mmol). The solution was stirred overnight. The reaction mixture was extracted with 2N HCl. The resulting acidic aqueous solution was made basic by adding 2N NaOH. The combined basic aqueous solution was extracted with DCM. The organic phase was washed with brine, dried and concentrated giving the title compound (11.5 g, 69%). 1H NMR (DMSO-D6): δ 1.66 (4H, m), 2.49 (4H, m), 2.75 (2H, t, J=6.0 Hz), 3.72 (3H, s), 4.00 (2H, t, J=6.0 Hz), 6.94 (1H, d, J=8.6 Hz), 7.14 (1H, d, J=8.6 Hz), 7.79 (1H, d, J=8.1 Hz), 7.94 (1H, d, J=8.1 Hz), 8.23 (1H, s), 10.55 (1H, s). LCMS m/z=420 (m+H+).

後処理

  1. extractionThe reaction mixture was extracted with 2N HCl
  2. additionby adding 2N NaOH
  3. extractionThe combined basic aqueous solution was extracted with DCM
  4. washThe organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-a822c74cca6540a7be14b399ff1e7a18
出典データセット
uspto-grants-2007_10
特許番号
US07285557B2

反応ノート

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