Benzenesulfenyl chloride → HCID 53892721, compound

HRID 1613451Notes

Reaction equation

HRID 1613451 reaction equation
[C:1]1([S:7]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:9][C:10]1[CH:11]=[C:12]([CH:30]=[CH:31][CH:32]=1)[O:13][C:14]1[CH:29]=[CH:28][C:17]([O:18][CH2:19][CH:20]([NH:22][C:23](=[O:27])[O:24][CH2:25][CH3:26])[CH3:21])=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.N1C=CC=CC=1>[C:1]1([S:7][N:22]([CH:20]([CH3:21])[CH2:19][O:18][C:17]2[CH:28]=[CH:29][C:14]([O:13][C:12]3[CH:30]=[CH:31][CH:32]=[C:10]([Cl:9])[CH:11]=3)=[CH:15][CH:16]=2)[C:23](=[O:27])[O:24][CH2:25][CH3:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 11008040Benzenesulfenyl chlorideHCID 53780935HCID 53780935, compound

Product 1

HCID 53892721HCID 53892721, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

A solution of 4 g of phenylsulfenyl chloride in 10 ml of toluene is added dropwise at 0°-5° C. in the course of 20 minutes to a solution of 9 g of ethyl 2-[4-(3-chlorophenoxy)phenoxy]-1-methylethylcarbamate in 30 ml of pyridine, with stirring, and the mixture is stirred for a further 15 hours at room temperature. Most of the pyridine and toluene is then distilled off in vacuo at a temperature of lower than 45° C., and the residue is poured into 300 ml of ice-water and extracted repeatedly with ether. The combined ether phases are first washed with cold, dilute hydrochloric acid and then with water, the mixture is dried over sodium sulfate, and the solvent is distilled off completely. The residue is purified further by chromatography on silica gel (eluent: n-hexane/diethyl ether, 19:1), by which process ethyl N-phenylthio-2-[4-(3-chlorophenoxy)phenoxy]-1-methylethylcarbamate is obtained as a colourless oil, nD20 : 1.5810.

Workup

  1. stirringthe mixture is stirred for a further 15 hours at room temperature
  2. distillationMost of the pyridine and toluene is then distilled off in vacuo at a temperature of lower than 45° C.
  3. additionthe residue is poured into 300 ml of ice-water
  4. extractionextracted repeatedly with ether
  5. washThe combined ether phases are first washed with cold, dilute hydrochloric acid
  6. dry with materialwith water, the mixture is dried over sodium sulfate
  7. distillationthe solvent is distilled off completely
  8. customThe residue is purified further by chromatography on silica gel (eluent: n-hexane/diethyl ether, 19:1), by which process ethyl N-phenylthio-2-[4-(3-chlorophenoxy)phenoxy]-1-methylethylcarbamate
  9. customis obtained as a colourless oil, nD20

Sources & evidence

ORD record
ord-4f7809e0335c4e66a2a86b5b1ba303a9
Source dataset
uspto-grants-1993_03
Patent number
US05192803

Reaction notes

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