Bicarbonate Ion → Benzenamine, 2-bromo-4-(4-morpholinyl)-6-(trifluoromethyl)-

HRID 1867282ノート

反応式

HRID 1867282 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:3]=1[NH2:13].Br[CH2:15][CH2:16][O:17][CH2:18][CH2:19]Br.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:3]=1[NH2:13]

参加物

6

反応物 4

HCID 769Bicarbonate IonHCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 674076781,4-Benzenediamine, 2-bromo-6-(trifluoromethyl)-

生成物 1

HCID 67405904Benzenamine, 2-bromo-4-(4-morpholinyl)-6-(trifluoromethyl)-収率 63%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Bromo-6-trifluoromethyl-benzene-1,4-diamine (2.21 g), bis-(2-bromoethyl)ether (1.30 mL) and N,N-diisopropyl-ethylamine (4.64 mL) were mixed in N,N-dimethylformamide (19 mL) and healed to 180° C. for 30 minutes in a sealed microwave process vial. Saturated aqueous bicarbonate (100 mL) was added and the crude mixture was extracted with ethyl acetate (100 mL). The organic phase was washed with water (100 mL) and brine (100 mL), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 1.78 g (63%) of the title compound as a yellow solid. LC-MS (m/z) 326 (MH+); tR=2.54, (UV, ELSD) 83%, 75%. 1H NMR (500 MHz, DMSO-d6): 2.99 (m, 4H), 3.70 (m, 4H), 5.00 (s, 2H), 7.00 (d, 1H), 7.38 (d, 1H).

後処理

  1. extractionthe crude mixture was extracted with ethyl acetate (100 mL)
  2. washThe organic phase was washed with water (100 mL) and brine (100 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-2cfd2cf31fb542559f55383a86019131
出典データセット
uspto-grants-2009_12
特許番号
US07632835B2

反応ノート

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