2-Iodo-4-nitroaniline → 2-(3,5-Dimethylphenylethynyl)-4-nitrophenylamine

HRID 1292395노트

반응식

HRID 1292395 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]#[CH:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.I[C:12]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:13]=1[NH2:14]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][C:12]2[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:13]=2[NH2:14])[CH:5]=[C:6]([CH3:8])[CH:7]=1

참가 물질

4

반응물 2

HCID 2226292-Iodo-4-nitroanilineHCID 64326111-Ethynyl-3,5-dimethylbenzene

생성물 1

HCID 189142732-(3,5-Dimethylphenylethynyl)-4-nitrophenylamine

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

실험 절차

To a solution of 3,5-dimethylphenylethyne (156 mg in 7 mL of dry, nitrogen saturated triethylamine) was added 2-iodo-4-nitroaniline (264 mg, prepared essentially as described in: Toth, I. Helv. Chim. Acta, 1971, 54, 1486.) followed by tetrakis(triphenylphosphine)palladium (23 mg) and cuprous bromide (10 mg) and the mixture heated to reflux on an oil bath. After 2 hours the mixture was cooled to room temperature, concentrated in vacuo and purified by flash chromatography on silica gel (hexane:methylene chloride:ethyl acetate, 15:8:1) to give the title compound (256 mg).

후처리

  1. customprepared essentially
  2. temperaturethe mixture heated
  3. temperatureto reflux on an oil bath
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography on silica gel (hexane:methylene chloride:ethyl acetate, 15:8:1)

출처 및 근거

ORD 기록
ord-3b90f590687e4e068ae06cc3c3fd3d13
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05756507

반응 노트

불러오는 중…