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

HRID 1672950Notes

Reaction equation

[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

Participants

Conditions

Temperature: 50 °C

Procedure

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+).

Workup

temperatureThe mixture was refluxed for 2 h
concentrationconcentrated in vacuo to dryness
temperaturecooled to room temperature
additionTo the residue was added ethanol
temperaturethe mixture was refluxed for several minutes
temperaturecooled to room temperature
filtrationlight blue crystalline product was filtered off
customdried in vacuo

Sources & evidence

ORD record: ord-514382cad36f46d48d56cac4bd63c2c9
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999006B2

Reaction notes

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