Chloranil → Methyl 4-[(2-fluoro-4-iodophenyl)amino]thiophene-3-carboxylate

HRID 1672950노트

반응식

HRID 1672950 반응식
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH2:14][S:13][CH2:12][C:11]=1[C:15]([O:17][CH3:18])=[O:16].ClC1C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][S:13][CH:14]=1

참가 물질

4

반응물 2

HCID 8371ChloranilHCID 67051651Methyl 4-[(2-fluoro-4-iodophenyl)amino]-2,5-dihydrothiophene-3-carboxylate

생성물 1

HCID 66617354Methyl 4-[(2-fluoro-4-iodophenyl)amino]thiophene-3-carboxylate수율 62.1%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
50 °C

실험 절차

To a mixture of methyl 4-[(2-fluoro-4-iodophenyl)amino]-2,5-dihydrothiophene-3-carboxylate (1.2 g, 3.16 mmol) in 10 ml of anhydrous toluene was added 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione (0.78 g, 3.16 mmol). The mixture was refluxed for 2 h. The mixture was cooled to 50° C. and concentrated in vacuo to dryness and cooled to room temperature. To the residue was added ethanol and the mixture was refluxed for several minutes, cooled to room temperature and light blue crystalline product was filtered off and dried in vacuo to afford methyl 4-[(2-fluoro-4-iodophenyl)amino]thiophene-3-carboxylate (0.74 g, 62%). 1HNMR (d6-DMSO): 8.78 (s, 1H), 8.42 (d, 1H), 7.64 (d, 1H), 7.46 (d, 1H), 7.37 (t, 1H), 7.14 (s, 1H), 3.85 (s, 3H); MS (EI) for C12H9FINO2S: 378 (MH+).

후처리

  1. temperatureThe mixture was refluxed for 2 h
  2. concentrationconcentrated in vacuo to dryness
  3. temperaturecooled to room temperature
  4. additionTo the residue was added ethanol
  5. temperaturethe mixture was refluxed for several minutes
  6. temperaturecooled to room temperature
  7. filtrationlight blue crystalline product was filtered off
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-514382cad36f46d48d56cac4bd63c2c9
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07999006B2

반응 노트

불러오는 중…