Ethanethiol → tert-Butyl 3-(ethylthio)propylcarbamate

HRID 1371398Notes

Reaction equation

HRID 1371398 reaction equation
Br[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[CH2:13]([SH:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:13]([S:15][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:14]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamate

Product 1

HCID 23089241tert-Butyl 3-(ethylthio)propylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl 3-bromopropylcarbamate (0.30 g) in N,N-dimethylformamide (5 ml) was treated with ethanethiol (0.104 ml) and potassium carbonate (0.29 g), and the mixture stirred at room temperature overnight. The mixture was partitioned between water (20 ml) and dichloromethane (30 ml), and the organic layers evaporated in vacuo to give the title compound (0.236 g).

Workup

  1. customThe mixture was partitioned between water (20 ml) and dichloromethane (30 ml)
  2. customthe organic layers evaporated in vacuo

Sources & evidence

ORD record
ord-0d850811e84249cead6d26508b5c1581
Source dataset
uspto-grants-2007_01
Patent number
US07157457B2

Reaction notes

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