p-Toluenesulfonic acid → HCID 57079753, compound

HRID 1680155Notes

Reaction equation

HRID 1680155 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:9](=O)[CH2:8][CH2:7][S:6]1)=[O:4].[Cl:11][C:12]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:14][C:13]1[CH:15]=[CH:16][CH:17]=[C:18]([CH3:19])[C:12]=1[Cl:11])=[O:4]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8371ChloranilHCID 1028702-Thiophenecarboxylic acid, tetrahydro-3-oxo-, methyl esterHCID 114124382-Chloro-m-toluidine

Product 1

HCID 57079753HCID 57079753, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

15.9 g (0.1 mole) of 3-oxotetrahydro-2-thiophencarboxylic acid methyl ester, 14.2 g of 2-chloro-3-methylaniline and 200 mg of p-toluenesulfonic acid are heated in 500 ml of toluene for six hours using a water separator. 24.6 g (0.1 mole) of chloranil are then added, and the mixture is boiled for a further one hour. It is cooled and filtered; the filtrate is washed with 100 ml each of 2 N sodium hydroxide solution, sodium dithionite solution and water and concentrated; the residue is purified by column chromatography (silica gel, toluene/ethyl acetate 4/1). 3-(2-Chloro-3-methylanilino)-2-thiophencarboxylic acid methyl ester is obtained as an oil.

Workup

  1. temperatureIt is cooled
  2. filtrationfiltered
  3. washthe filtrate is washed with 100 ml each of 2 N sodium hydroxide solution, sodium dithionite solution and water
  4. concentrationconcentrated
  5. customthe residue is purified by column chromatography (silica gel, toluene/ethyl acetate 4/1)

Sources & evidence

ORD record
ord-959ec5e2feab4efabbe96fc7c4c88099
Source dataset
uspto-grants-1981_06
Patent number
US04272507

Reaction notes

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