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Methyl Methanesulfonate → HCID 19819114, compound

HRID 1195420
Notes
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Reaction equation

HRID 1195420 reaction equation
Cl[CH2:2][CH2:3][N:4]=[C:5]=[O:6].[CH3:7][S:8]([O:11]C)(=[O:10])=[O:9]>CS([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[N:4]([CH2:3][CH2:2][O:11][S:8]([CH3:7])(=[O:10])=[O:9])=[C:5]=[O:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4156Methyl Methanesulfonate2×HCID 160352-Chloroethyl isocyanate2×

Product 1

HCID 19819114HCID 19819114, compound

Reagents, catalysts & solvents 1

HCID 30176031-Butanaminium, N,N,N-tributyl-, methanesulfonate (1:1)Catalyst

Conditions

Temperature
120 °C

Procedure

20.0 g (0.06 mol) of tetrabutylammonium methanesulfonate are added to a solution of 36.0 g (0.34 mol) of 2-chloroisocyanatoethane and 93.3 g (0.85 mol) of methyl methanesulfonate and the mixture is heated at 120° C for 6 hours. It is distilled in a thin layer evaporator at 180° C. under a pressure of 0.04 mbar and the crude product is purified by distillation. 18.0 g (0.17 mol) of 2chloroisocyanatoethane and 71.0 g (0.65 mol) of methyl methanesulfonate are recovered in this way.

Workup

  1. distillationIt is distilled in a thin layer evaporator at 180° C. under a pressure of 0.04 mbar
  2. distillationthe crude product is purified by distillation

Sources & evidence

ORD record
ord-d433e79b626e43a59a3c9c476aee80f4
Source dataset
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05110975

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes