Methanol → methyl N-(2-chloroacetyl)carbamate

HRID 27411

Reaction equation

HRID 27411 reaction equation
[Cl:1][CH2:2][C:3]([NH2:5])=[O:4].[C:6](Cl)(=[O:10])C(Cl)=O.[CH3:12][OH:13]>ClCCCl>[CH3:12][O:13][C:6](=[O:10])[NH:5][C:3](=[O:4])[CH2:2][Cl:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 6580ChloroacetamideHCID 65578Oxalyl chloride

Product 1

HCID 518783methyl N-(2-chloroacetyl)carbamate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 2-chloroacetamide (122.6 g, 1.31 mol) in 300 ml of 1,2-dichloroethane is cooled to 0° C. and treated with oxalyl chloride (200 g, 1.57 mol). The reaction mixture is heated at reflux for 4 hours. After cooling to 5° C., 68 ml of MeOH is added dropwise while keeping the internal temperature below 15° C. with external cooling. After addition is complete, the product is separated by filtration and washed with CH2Cl2 and Et2O. Recrystallization from CH2Cl2 yields methyl(chloroacetyl)carbamate.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 4 hours
  3. temperatureAfter cooling to 5° C.
  4. customthe internal temperature below 15° C.
  5. additionAfter addition
  6. customthe product is separated by filtration
  7. washwashed with CH2Cl2 and Et2O
  8. customRecrystallization from CH2Cl2

Sources & evidence

ORD record
ord-93e933a150fd4dfdad3e601d64c283ad
Source dataset
uspto-grants-1980_09
Patent number
US04221796

Linked notes

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