1-Octanethiol → HCID 85799362, compound

HRID 985624Notes

Reaction equation

HRID 985624 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([O:17][CH3:18])(=[O:16])[CH2:14][SH:15].[CH2:19]([SH:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>ClCCl>[CH3:18][O:17][C:13]([CH2:14][S:15][S:27][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:16]

Participants

5

Reactant 3

HCID 81441-OctanethiolHCID 16907Methyl ThioglycolateHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 85799362HCID 85799362, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

In a N2 purged flask there was dissolved Diethyl azodicarboxylate (5.0 g, 28.71 mmol) in dichloromethane (150 mL). A solution of Methyl thioglycolate (2.89 g, 27.27 mmol) in dichloromethane (50 mL) was then added dropwise at room temperature over 20 minutes. After 1.5 hours stirring, a solution of octanethiol (4.8 mL, 27.27 mmol) in dichloromethane (50 mL) was added dropwise over 20 minutes, and the resulting solution was stirred for an additional 12 hours at room temperature. The solvent was then removed under reduced pressure, and the resulting oil was then purified over flash silica with 5% ethyl acetate in hexanes to yield MeOC(O)CH2SSC8H17 as a clear, colorless oil.

Workup

  1. stirringthe resulting solution was stirred for an additional 12 hours at room temperature
  2. customThe solvent was then removed under reduced pressure
  3. customthe resulting oil was then purified over flash silica with 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6476377158e949b8a5b1b1bdcda88788
Source dataset
uspto-grants-2005_03
Patent number
US06872804B2

Reaction notes

Loading…