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

HRID 1613445Notes

Reaction equation

HRID 1613445 reaction equation
[C:1]1([S:7]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:9][C:10]1[CH:11]=[C:12]([CH:29]=[C:30]([F:32])[CH:31]=1)[O:13][C:14]1[CH:28]=[CH:27][C:17]([O:18][CH2:19][CH2:20][NH:21][C:22](=[O:26])[O:23][CH2:24][CH3:25])=[CH:16][CH:15]=1.Cl>C1(C)C=CC=CC=1.N1C=CC=CC=1>[C:1]1([S:7][N:21]([CH2:20][CH2:19][O:18][C:17]2[CH:16]=[CH:15][C:14]([O:13][C:12]3[CH:29]=[C:30]([F:32])[CH:31]=[C:10]([F:9])[CH:11]=3)=[CH:28][CH:27]=2)[C:22](=[O:26])[O:23][CH2:24][CH3:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11008040Benzenesulfenyl chlorideHCID 13502190Ethyl 2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate

Product 1

HCID 19775874ethyl N-phenylthio-2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

5.7 g of freshly distilled phenylsulfenyl chloride in 10 ml of toluene are 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 4 more hours at room temperature. The reaction mixture is poured into 300 ml of 2N hydrochloric acid and ice, and the mixture is extracted twice using diethyl ether. The combined organic phases are washed to neutrality with water and sodium chloride solution 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, 20:1), which gives pure ethyl N-phenylthio-2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate, nD20 : 1.5700.

Workup

  1. stirringAfter this, the mixture is stirred for 4 more hours at room temperature
  2. extractionthe mixture is extracted twice using diethyl ether
  3. washThe combined organic phases 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, 20:1), which

Sources & evidence

ORD record
ord-1aa673f0546042899966545ca3e52327
Source dataset
uspto-grants-1993_03
Patent number
US05192803

Reaction notes

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