p-Toluenesulfonic acid → HCID 57226000, compound

HRID 1680154Notes

Reaction equation

HRID 1680154 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:9](=O)[CH2:8][S:7][CH2:6]1)=[O:4].[Cl:11][C:12]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:13]=1[NH2:14].C1(C)C=CC(S(O)(=O)=O)=CC=1.BrBr.S([O-])([O-])=O.[Na+].[Na+]>ClC(Cl)C.O>[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:14][C:13]2[C:12]([Cl:11])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:19])=[CH:8][S:7][CH:6]=1)=[O:4]

Participants

8

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 118462,6-DichloroanilineHCID 24408BromineHCID 24437Sodium SulfiteHCID 984243-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl ester

Product 1

HCID 57226000HCID 57226000, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent2×

Procedure

15.9 g (0.1 mole) of 4-oxotetrahydro-3-thiophencarboxylic acid methyl ester, 17.5 g of 2,6-dichloroaniline and 200 mg of p-toluenesulfonic acid are heated in 500 ml of dichloroethane for six hours using a water separator. The solution is cooled to -25° and 52.5 g of bromine in 100 ml of dichloroethane are added dropwise. The mixture is stirred for a further 5 minutes; 100 ml of 10 percent strength (aq) sodium sulfite solution are added thereto, and the organic phase is separated off, washed with water and a sodium carbonate solution, dried and concentrated. Pure 4-(2,6-dichloroanilino)-3-thiophencarboxylic acid methyl ester is obtained after a bulb tube distillation (bp. 140°/10-2Pascal).

Workup

  1. temperatureThe solution is cooled to -25°
  2. customthe organic phase is separated off
  3. washwashed with water
  4. dry with materiala sodium carbonate solution, dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e09570e134884e70af1a2f92a1792a18
Source dataset
uspto-grants-1981_06
Patent number
US04272507

Reaction notes

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