Methanol → methyl N-(2-chloroacetyl)carbamate
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureThe reaction mixture is heated
- temperatureat reflux for 4 hours
- temperatureAfter cooling to 5° C.
- customthe internal temperature below 15° C.
- additionAfter addition
- customthe product is separated by filtration
- washwashed with CH2Cl2 and Et2O
- customRecrystallization from CH2Cl2
Sources & evidence
- ORD record
- ord-93e933a150fd4dfdad3e601d64c283ad
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04221796
Reaction notes
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