3-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl ester → Methyl-4-(2-fluoro-4-iodo-phenylamino)-2,3-dihydro-thiophene-3-carboxylate

HRID 237349

Reaction equation

HRID 237349 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:9](=O)[CH2:8][S:7][CH2:6]1)=[O:4].[F:11][C:12]1[CH:18]=[C:17]([I:19])[CH:16]=[CH:15][C:13]=1[NH2:14]>C(O)C.C(O)(=O)C>[CH3:1][O:2][C:3]([CH:5]1[C:9]([NH:14][C:13]2[CH:15]=[CH:16][C:17]([I:19])=[CH:18][C:12]=2[F:11])=[CH:8][S:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 984243-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl esterHCID 1856942-Fluoro-4-iodoaniline

Product 1

HCID 66617580Methyl-4-(2-fluoro-4-iodo-phenylamino)-2,3-dihydro-thiophene-3-carboxylateYield 42%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of methyl-4-oxo-tetrahydro-thiophene-3-carboxylate (5.75 g, 35.9 mmol) and 2-fluoro-4-iodo-aniline (9.4 g, 40.9 mmol) were heated to reflux in a mixture of ethanol (25 mL) and acetic acid (0.3 mL) for 18 hours. The solution was cooled to room temperature, filtered and the solid product dried in vacuo to provide methyl-4-(2-fluoro-4-iodo-phenylamino)-2,3-dihydro-thiophene-3-carboxylate (5.70 g, 42% yield). MS (EI) for C12H11FINO2S: 380 (MH+).

Workup

  1. filtrationfiltered
  2. customthe solid product dried in vacuo

Sources & evidence

ORD record
ord-2b0c61ca66c2446087e7accda5ed23b4
Source dataset
uspto-grants-2014_02
Patent number
US08642584B2

Linked notes

Loading…