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

HRID 1158677노트

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HRID 1158677 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
180 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a87f38e82e064a89adb5c38aa5764741
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812023B2

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