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

HRID 1672950ノート

反応式

HRID 1672950 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
50 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-514382cad36f46d48d56cac4bd63c2c9
出典データセット
uspto-grants-2011_08
特許番号
US07999006B2

反応ノート

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