Hydrochloric Acid → ethyl N-(4-chlorophenylthio)-2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate

HRID 1613446Notes

Reaction equation

HRID 1613446 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]Cl)=[CH:4][CH:3]=1.[F:10][C:11]1[CH:12]=[C:13]([CH:30]=[C:31]([F:33])[CH:32]=1)[O:14][C:15]1[CH:29]=[CH:28][C:18]([O:19][CH2:20][CH2:21][NH:22][C:23](=[O:27])[O:24][CH2:25][CH3:26])=[CH:17][CH:16]=1.Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][N:22]([CH2:21][CH2:20][O:19][C:18]2[CH:17]=[CH:16][C:15]([O:14][C:13]3[CH:30]=[C:31]([F:33])[CH:32]=[C:11]([F:10])[CH:12]=3)=[CH:29][CH:28]=2)[C:23](=[O:27])[O:24][CH2:25][CH3:26])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 110844654-ChlorobenzenesulfenylchlorideHCID 13502190Ethyl 2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate

Product 1

HCID 19775881ethyl N-(4-chlorophenylthio)-2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7.6 g of freshly distilled 4-chlorophenylsulfenyl chloride is added dropwise at 0° to +5° C. in the course of 30 minutes to a solution of 12 g of ethyl 2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate in 40 ml of pyridine, with stirring. After this, the mixture is stirred for 16 more hours at room temperature. The reaction mixture is poured into 200 ml of 2N hydrochloric acid and ice, and the mixture is extracted twice using diethyl ether. The combined ether extracts are washed to neutrality with water and dried over sodium sulfate. The solvent is distilled off in vacuo, and the residue is purified by chromatography on silica gel (eluent: hexane/diethyl ether, 9:1), which gives pure ethyl N-(4-chlorophenylthio)-2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate, nD20 1.5763.

Workup

  1. stirringAfter this, the mixture is stirred for 16 more hours at room temperature
  2. extractionthe mixture is extracted twice using diethyl ether
  3. washThe combined ether extracts are washed
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent is distilled off in vacuo
  6. customthe residue is purified by chromatography on silica gel (eluent: hexane/diethyl ether, 9:1), which

Sources & evidence

ORD record
ord-e789ff9d797a4a38b05860a379f6ec3c
Source dataset
uspto-grants-1993_03
Patent number
US05192803

Reaction notes

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