Dicyclohexylcarbodiimide → N-[2-chloro-5-(o-chloro-p-trifluoromethyl-phenoxy)-benzoyl]-S,S-dimethyl-sulphoximine

HRID 637250Notes

Reaction equation

HRID 637250 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[Cl:22])=[CH:7][C:3]=1[C:4](O)=[O:5].C1(N=C=NC2CCCCC2)CCCCC1.[CH3:38][S:39]([CH3:42])(=[NH:41])=[O:40]>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[Cl:22])=[CH:7][C:3]=1[C:4]([N:41]=[S:39]([CH3:42])([CH3:38])=[O:40])=[O:5]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 123119Sulfoximine, S,S-dimethyl-HCID 130136822-Chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoic acid

Product 1

HCID 20256526N-[2-chloro-5-(o-chloro-p-trifluoromethyl-phenoxy)-benzoyl]-S,S-dimethyl-sulphoximine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.46 g of 2-chloro-5-(o-chloro-p-trifluoromethyl-phenoxy)-benzoic acid in 20 ml of methylene chloride is added dropwise at room temperature while stirring to a solution of 1.3 g of dicyclohexylcarbodiimide and 0.6 g of dimethyl sulphoximine in 5 ml of methylene chloride, a slight exothermic reaction occurring. After a reaction time of 15 minutes the solvent is removed by evaporation under reduced pressure and the residue is purified by chromatography on silica gel with n-hexane/ethyl acetate (9:1). The white crystalline product is then recrystallized from methylene chloride/n-hexane. There is obtained N-[2-chloro-5-(o-chloro-p-trifluoromethyl-phenoxy)-benzoyl]-S,S-dimethyl-sulphoximine, m.p. 128°-131° C.; mass spectrum: m/e 425/427; 1H-NMR (CDCl3): 7.8-6.9 (m,6H), 3.4 (s,6H).

Workup

  1. customa slight exothermic reaction
  2. customAfter a reaction time of 15 minutes the solvent is removed by evaporation under reduced pressure
  3. customthe residue is purified by chromatography on silica gel with n-hexane/ethyl acetate (9:1)
  4. customThe white crystalline product is then recrystallized from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-f94b5adc1f5d4eff8388a79f4913dbd5
Source dataset
uspto-grants-1985_12
Patent number
US04556413

Reaction notes

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