Dichloromethane → HCID 767171, compound

HRID 1090095Notes

Reaction equation

HRID 1090095 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-8d5b6bce266744dab7e9d7c3e1625958
Source dataset
uspto-grants-1992_01
Patent number
US05081125

Reaction notes

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