p-Chlorothiophenol → tert-Butyl 3-[(4-chlorophenyl)thio]propylcarbamate

HRID 1677004Notes

Reaction equation

HRID 1677004 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].CS(O[CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])(=O)=O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:21])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7815p-ChlorothiophenolHCID 24758Sodium hydrideHCID 114141093-((Tert-butoxycarbonyl)amino)propyl methanesulfonate

Product 1

HCID 85937154tert-Butyl 3-[(4-chlorophenyl)thio]propylcarbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-chlorothiophenol (91 mg) in 6 mL of DMF was cooled to 0° C. under N2. Sodium hydride (60%, 30 mg) was added and the reaction stirred for 30 minutes. The product from Step A above in 3 mL of DMF was added and the reaction allowed to warm to room temperature while stirring overnight. This was diluted with EtOAc, washed with saturated NaHCO3 and brine and dried over Na2SO4. Concentrating in vacuo gave the titled compound. ESI+ MS: 202 [MH-Boc]+.

Workup

  1. stirringwhile stirring overnight
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationConcentrating in vacuo

Sources & evidence

ORD record
ord-862579fe7cc14c6ba70f67a95570f4a6
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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