3,4-dihydro-2H-pyran → Methyl (2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)carbamodithioate

HRID 1980371Notes

Reaction equation

HRID 1980371 reaction equation
[CH3:1][S:2][C:3](=[S:8])[NH:4][CH2:5][CH2:6][OH:7].[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1>ClCCl.C(=O)([O-])O.[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][S:2][C:3](=[S:8])[NH:4][CH2:5][CH2:6][O:7][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][O:9]1

Participants

6

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 13277332Methyl (2-hydroxyethyl)carbamodithioate

Product 1

HCID 54082931Methyl (2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)carbamodithioateYield 101.5%

Reagents, catalysts & solvents 3

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of N-(2-hydroxyethyl)dithiocarbamic acid methyl ester (81.7 g) in dichloromethane (300 ml) are added dihydropyran (54 g) and toluene-p-sulfonic acid monohydrate (1.0 g), and the mixture is stirred for 1 hour. The reaction mixture is poured in aqueous sodium hydrogen carbonate, shaken and the resulting organic layer is separated. The layer is concentrated under reduced pressure to give N-[2-(2-tetrahydropyranyl)oxyethyl]dithiocarbamic acid methyl ester (129 g).

Workup

  1. stirringshaken
  2. customthe resulting organic layer is separated
  3. concentrationThe layer is concentrated under reduced pressure

Sources & evidence

ORD record
ord-34dd4e80b2bb436e821b2d27aa80360f
Source dataset
uspto-grants-1985_04
Patent number
US04508909

Reaction notes

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