Bicarbonate Ion → 2-Amino-3-chloro-5-morpholin-4-yl-benzonitrile

HRID 905569ノート

反応式

HRID 905569 の反応式
[NH2:1][C:2]1[C:9]([Cl:10])=[CH:8][C:7]([NH2:11])=[CH:6][C:3]=1[C:4]#[N:5].Br[CH2:13][CH2:14][O:15][CH2:16][CH2:17]Br.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-]>CN(C)C=O>[NH2:1][C:2]1[C:9]([Cl:10])=[CH:8][C:7]([N:11]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:6][C:3]=1[C:4]#[N:5]

参加物

6

反応物 4

HCID 769Bicarbonate IonHCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 137997002,5-Diamino-3-chlorobenzonitrile

生成物 1

HCID 674078362-Amino-3-chloro-5-morpholin-4-yl-benzonitrile収率 91%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
180 °C

実験手順

2,5-Diamino-3-chloro-benzonitrile (387 mg), bis-(2-bromoethyl)ether (0.35 mL) and N,N-diisopropyl-ethylamine (1.25 mL) were mixed in N,N-dimethylformamide (4 mL) and heated to 180° C. for 30 minutes in a sealed microwave process vial. Saturated aqueous bicarbonate (20 mL) was added and the crude mixture was extracted with ethyl acetate (20 mL). The organic phase was washed with water (20 mL) and brine (20 mL), dried over sodium sulfate and concentrated in vacuo to furnish 0.50 g (91%) of the title compound as a brown solid. LC-MS (m/z) 238 (MH+); tR=2.31, (UV, ELSD) 85%, 95%. 1H NMR (500 MHz, DMSO-d6): 2.97 (m, 4H), 3.69 (m, 4H), 5.59 (s, 2H), 7.04 (d, 1H), 7.29 (d, 1H).

後処理

  1. extractionthe crude mixture was extracted with ethyl acetate (20 mL)
  2. washThe organic phase was washed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6f6a3a8cbd9940a58d78ad6338b4a231
出典データセット
uspto-grants-2011_09
特許番号
US08012962B2

反応ノート

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