Sulfuric Acid → Methyl (2-tert-butoxyethyl)carbamodithioate

HRID 1980370Notes

Reaction equation

HRID 1980370 reaction equation
[CH3:1][S:2][C:3](=[S:8])[NH:4][CH2:5][CH2:6][OH:7].[CH2:9]=[C:10]([CH3:12])[CH3:11].S(=O)(=O)(O)O.[OH-].[Na+]>ClCCl>[CH3:1][S:2][C:3](=[S:8])[NH:4][CH2:5][CH2:6][O:7][C:10]([CH3:12])([CH3:11])[CH3:9]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 14798Sodium HydroxideHCID 13277332Methyl (2-hydroxyethyl)carbamodithioate

Product 1

HCID 54386052Methyl (2-tert-butoxyethyl)carbamodithioate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a sealed glass tube is placed a solution of N-(2-hydroxyethyl)dithiocarbamic acid methyl ester (4.3 g), isobutene (30 ml) and concentrated sulfuric acid (0.1 ml) in dichloromethane (20 ml) prepared at -50° C. to -60° C. The mixture is warmed slowly to room temperature and then left to stand for 17 hours. The reaction mixture is poured into aqueous 0.5% sodium hydroxide and extracted with dichloromethane. The extract is washed with water, dried and concentrated to give N-(2-t-butoxyethyl)dithiocarbamic acid methyl ester.

Workup

  1. customIn a sealed glass tube is placed
  2. waitleft
  3. extractionextracted with dichloromethane
  4. washThe extract is washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3fe3f7d648c5425b934686ff83b468d6
Source dataset
uspto-grants-1985_04
Patent number
US04508909

Reaction notes

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