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

HRID 1717608노트

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HRID 1717608 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%). 1H NMR (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-b9cf38bcc49c46deb34a4272c1884b2e
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803839B2

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