Dichloromethane → HCID 767171, compound

HRID 654461Notes

Reaction equation

HRID 654461 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([NH2:22])=[C:17]([CH:21]=1)[C:18]([OH:20])=[O:19].C(Cl)Cl>N1C=CC=CC=1>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([NH:22][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[C:17]([CH:21]=1)[C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 73984-Chlorobenzenesulfonyl chlorideHCID 124762-Amino-5-chlorobenzoic acid

Product 1

HCID 767171HCID 767171, compoundYield 115.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.0 g of 4-chlorobenzenesulfonic acid chloride are added to a solution of 3.8 g of 5-chloro-2-aminobenzoic acid [4-(3-chloro-5-trifluoromethylpyridyl-2-oxy)-anilide] in 8.6 ml of pyridine at 0° C. After the reaction mixture has been stirred for 16 hours at room temperature, 300 ml of methylene chloride are added and the resulting solution is then washed with 100 ml each of 1N HCl, H2O, saturated NaHCO3 solution and saturated NaCl solution. The organic phase is then dried with MgSO4 and concentrated by evaporation. The crude product obtained is purified by stirring in diethyl ether. In this manner 3.8 g of 5-chloro-2-[(4-chlorophenylsulfonyl)-amino]-benzoic acid [4-(3-chloro-5-trifluoromethylpyridyl-2-oxy)-anilide] are obtained in the form of white crystals (m.p. 191°-193° C.).

Workup

  1. washthe resulting solution is then washed with 100 ml each of 1N HCl, H2O, saturated NaHCO3 solution and saturated NaCl solution
  2. dry with materialThe organic phase is then dried with MgSO4
  3. concentrationconcentrated by evaporation
  4. customThe crude product obtained
  5. customis purified
  6. stirringby stirring in diethyl ether

Sources & evidence

ORD record
ord-c71ada4a14c344979235be517451be38
Source dataset
uspto-grants-1992_07
Patent number
US05132314

Reaction notes

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