Nitrogen → 2',3',4'-Trimethoxy-biphenyl-3-carboxylic acid (2-bromo-5-nitro-phenyl)-amide

HRID 1944270

반응식

HRID 1944270 반응식
N#N.[CH3:3][O:4][C:5]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21](Cl)=[O:22])[CH:16]=1.[Br:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][C:26]=1[NH2:34]>ClCCl.N1C=CC=CC=1>[Br:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][C:26]=1[NH:34][C:21]([C:17]1[CH:16]=[C:15]([C:6]2[CH:7]=[CH:8][C:9]([O:13][CH3:14])=[C:10]([O:11][CH3:12])[C:5]=2[O:4][CH3:3])[CH:20]=[CH:19][CH:18]=1)=[O:22]

참가 물질

6

반응물 3

HCID 947NitrogenHCID 826072-Bromo-5-nitroanilineHCID 161162872',3',4'-Trimethoxy-biphenyl-3-carbonyl chloride

생성물 1

HCID 597857012',3',4'-Trimethoxy-biphenyl-3-carboxylic acid (2-bromo-5-nitro-phenyl)-amide

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

(The following reaction is done in an anhydrous N2 atmosphere.) Add a solution of 2′,3′,4′-trimethoxy-biphenyl-3-carbonyl chloride (35) (345 mg, 1.13 mmol) in dichloromethane (5 mL) to an ice cooled solution of 2-bromo-5-nitro-phenylamine (88) (232 mg, 1.07 mmol) in anhydrous dichloromethane (12 mL) and anhydrous pyridine (2.9 mL). Stir the reaction mixture for 15 min at 0° C. and additional 17 h at rt. Pour the reaction mixture into ice cooled 1M aqu. HCl (to get pH ca. 3), extract with EtOAc (3×), wash the combined organic layer with brine and dry it with Na2SO4 to afford crude 2′,3′,4′-trimethoxy-biphenyl-3-carboxylic acid (2-bromo-5-nitro-phenyl)-amide (89) as a beige solid (542 mg, quant.). NMR (400 MHz, CDCl3): 3.72 (s, 3H); 3.91 (s, 3H); 3.93 (s, 3H); 6.77 (d, 1H, J=8.6 Hz); 7.08 (d, 1H, J=8.6 Hz); 7.56 (t, 1H, J=8.8 Hz); 7.75 (d, 2H, J=8.8 Hz); 7.86 (d, 1H, J=8.8 Hz), 7.87 (d, 1H, J=8.8 Hz); 8.09 (t, 1H, J=1.7 Hz); 8.61 (br. s, 1H); 9.59 (d, 1H, J=2.5 Hz).

후처리

  1. custom(The following reaction
  2. customadditional 17 h
  3. customat rt
  4. additionPour the reaction mixture into ice
  5. temperaturecooled 1M aqu
  6. extractionHCl (to get pH ca. 3), extract with EtOAc (3×)
  7. washwash the combined organic layer with brine
  8. dry with materialdry it with Na2SO4

출처 및 근거

ORD 기록
ord-441c6aed3ced4584ae9ec240a7c22d3c
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394835B2

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