2-Mercaptoethanol → 2-[Methyl-phenyl-(2-sulfanylethoxy)silyl]oxyethanethiol

HRID 64396Notes

Reaction equation

HRID 64396 reaction equation
[CH3:1][Si:2]([CH3:11])([O:7][CH2:8][CH2:9][SH:10])[O:3][CH2:4][CH2:5][SH:6].C(N(CC)CC)C.ClC([SiH2][C:23]1[CH:28]=[CH:27]C=[CH:25][CH:24]=1)Cl.SCCO>CCOCC>[CH3:1][Si:2]([C:11]1[CH:27]=[CH:28][CH:23]=[CH:24][CH:25]=1)([O:3][CH2:4][CH2:5][SH:6])[O:7][CH2:8][CH2:9][SH:10]

Participants

6

Reactant 4

HCID 15672-MercaptoethanolHCID 8471TriethylamineHCID 57348665Dichloromethyl(phenyl)silaneHCID 716021552-[Dimethyl(2-sulfanylethoxy)silyl]oxyethanethiol

Product 1

HCID 867161642-[Methyl-phenyl-(2-sulfanylethoxy)silyl]oxyethanethiol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The 2-[methyl-phenyl-(2-sulfanylethoxy)silyl]oxyethanethiol (4) composition was synthesized according to the same procedure as 2-[dimethyl(2-sulfanylethoxy)silyl]oxyethanethiol (1), using triethylamine (5.02 g, 0.050 mol), dichloromethylphenylsilane (4.74 g, 0.025 mol), and 2-mercaptoethanol (3.88 g, 0.050 mol) in ether (500 mL). The 2-[methyl-phenyl-(2-sulfanylethoxy)silyl]oxyethanethiol (4) composition was obtained as a clear, colorless, foul-smelling liquid (6.30 g, 92.6%). The product was purified by distillation under reduced pressure and obtained as a clear, colorless, foul-smelling liquid (3.70 g, 54.4%), Bp=140-142° C. at 0.50 mmHg.

Workup

  1. customThe 2-[methyl-phenyl-(2-sulfanylethoxy)silyl]oxyethanethiol (4) composition was synthesized

Sources & evidence

ORD record
ord-68f280be8dc040f6bbe3adb2a31924df
Source dataset
uspto-grants-2016_09
Patent number
US09447124B2

Reaction notes

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