N-(5-Bromo-4-methoxy-2-nitrophenyl)acetamide → HCID 541150, 화합물

HRID 2406417노트

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HRID 2406417 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[O-:6].[K+].Br[C:14]1[CH:19]=[C:18]([NH:20][C:21]([CH3:23])=[O:22])[C:17]([N+:24]([O-:26])=[O:25])=[CH:16][C:15]=1[O:27][CH3:28]>CN(C=O)C.O>[NH:20]([C:18]1[C:17]([N+:24]([O-:26])=[O:25])=[CH:16][C:15]([O:27][CH3:28])=[C:14]([O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[CH:19]=1)[C:21]([CH3:23])=[O:22]

참가 물질

5

반응물 2

HCID 235991N-(5-Bromo-4-methoxy-2-nitrophenyl)acetamide2회HCID 23687391HCID 23687391, 화합물2회

생성물 1

HCID 541150HCID 541150, 화합물수율 79%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

To the above solid 7 under argon, was added a solution of 3.0 g (10.4 mmol) of bromide 6 in 20 mL of DMF via cannula. The resulting solution was stirred at 120° C. for 1 day. TLC and NMR indicated the presence of a small amount of starting material 6. The reaction solution was cooled to room temperature and 2 mmol of compound 7 was added. The solution was stirred at 120° C. for 12 hour, diluted with 200 mL of ice and water, and the solid was collected by filtration, washed with water, dried under vacuum, and crystallized from ethanol to give 3.04 g (79% yield) of compound 8. 1H NMR (CDCl3) δ 10.4 (s, 1 H, NH), 8.39 (s, 1 H), 7.83 (s, 1 H), 7.5 (m, 2 H), 7.3 (m, 2 H), 3.93 (s, 3 H, OMe), 2.23 (s, 3 H, CH3). 13C NMR (CDCl3) δ 174, 155.7, 153.9, 142.4, 141.6, 130.9, 123.0, 121.7, 121.6, (116.9, 116.8, 116.7, 116.6 q for CF3), 108.7, 106.6, 56.7, 21.8.

후처리

  1. temperatureThe reaction solution was cooled to room temperature
  2. stirringThe solution was stirred at 120° C. for 12 hour
  3. filtrationthe solid was collected by filtration
  4. washwashed with water
  5. customdried under vacuum
  6. customcrystallized from ethanol

출처 및 근거

ORD 기록
ord-f9490ddca1b440c9a1e1ed83a2f9cae1
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809368B2

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