Ethyl vinyl ether → Methyl [2-(1-ethoxyethoxy)ethyl]carbamodithioate

HRID 1980372Notes

Reaction equation

HRID 1980372 reaction equation
[CH3:1][S:2][C:3](=[S:8])[NH:4][CH2:5][CH2:6][OH:7].[CH2:9]([O:11][CH:12]=[CH2:13])[CH3:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(N(CC)CC)C>[CH3:1][S:2][C:3](=[S:8])[NH:4][CH2:5][CH2:6][O:7][CH:9]([O:11][CH2:12][CH3:13])[CH3:10]

Participants

5

Reactant 3

HCID 8023Ethyl vinyl etherHCID 521998p-Toluenesulfonic acid monohydrateHCID 13277332Methyl (2-hydroxyethyl)carbamodithioate

Product 1

HCID 53916168Methyl [2-(1-ethoxyethoxy)ethyl]carbamodithioate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To an ice cold and stirred mixture of N-(2-hydroxyethyl)dithiocarbamic acid methyl ester (1.513 g) and ethoxyethylene (1.92 ml) is added toluene-p-sulfonic acid monohydrate (9.5 mg). After stirring for 30 minutes at room temperature, the homogeneous solution is mixed with triethylamine (8 μl) and concentrated under reduced pressure to yield N-[2-(1-ethoxyethoxy)ethyl]dithiocarbamic acid methyl ester (2.4 g).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57111dd85ae14153bab335400f70264d
Source dataset
uspto-grants-1985_04
Patent number
US04508909

Reaction notes

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