Methanol → Methyl chlorosulfonylcarbamate

HRID 1742029Notes

Reaction equation

HRID 1742029 reaction equation
[CH3:1][OH:2].[Cl:3][S:4]([N:7]=[C:8]=[O:9])(=[O:6])=[O:5]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:8](=[O:9])[NH:7][S:4]([Cl:3])(=[O:6])=[O:5]

Participants

4

Reactant 2

HCID 887MethanolHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 10702364Methyl chlorosulfonylcarbamateYield 75.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of methanol (10.2 mL, 252 mmoles) in 15 mL toluene was added dropwise to a solution of chlorosulfonyl isocyanate (22.0 mL, 252 mmoles) in 75 mL toluene at 0° C. The cooling bath was removed and stirred for one-half hour at room temperature. This was then cooled to 0° C. and 65 mL ice cold hexanes was added. The white precipitate was collected by filtration and washed 2 times with a small amount of cold hexane to give 33.0 g of a white solid, mp 72°-74° C.

Workup

  1. customThe cooling bath was removed
  2. temperatureThis was then cooled to 0° C.
  3. addition65 mL ice cold hexanes was added
  4. filtrationThe white precipitate was collected by filtration
  5. washwashed 2 times with a small amount of cold hexane

Sources & evidence

ORD record
ord-1db662fa15d74a0196b40d7f8fb4edbf
Source dataset
uspto-grants-1994_08
Patent number
US05336690

Reaction notes

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