Chloroacetamide → tert-Butyl (2-chloroacetyl)carbamate

HRID 1667801Notes

Reaction equation

[Cl:1][CH2:2][C:3]([NH2:5])=[O:4].C(Cl)(=O)[C:7](Cl)=[O:8].[C:12]([OH:16])([CH3:15])([CH3:14])[CH3:13].ClCCCl.C(=O)([O-])O.[Na+]>ClCCCl>[Cl:1][CH2:2][C:3]([NH:5][C:7](=[O:8])[O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 2-chloroacetamide (25 g, 267 mmol) in 1,2-dichloroethane (125 mL) was added dropwise oxalyl chloride (28 mL, 321 mmol) at 0° C. After heating under reflux for 3 hr, the mixture was cooled to 0° C., tert-butyl alcohol/1,2-dichloroethane (75 mL, 1/1) was added to the mixture, and the mixture was stirred for 20 min. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture was extracted with 1,2-dichloroethane. After washing with saturated aqueous sodium hydrogencarbonate solution and water, the extract was dried over anhydrous magnesium sulfate and filtrated. The solvent was evaporated under reduced pressure, and the residue was recrystallized from cyclohexane to give the title compound (25.6 g, 49%) as white crystals.

Workup

temperatureAfter heating
temperatureunder reflux for 3 hr
extractionthe mixture was extracted with 1,2-dichloroethane
washAfter washing with saturated aqueous sodium hydrogencarbonate solution and water
dry with materialthe extract was dried over anhydrous magnesium sulfate
filtrationfiltrated
customThe solvent was evaporated under reduced pressure
customthe residue was recrystallized from cyclohexane

Sources & evidence

ORD record: ord-01d451c5fc2f4ba980cbe2f4c7bf9cd7
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044049B2

Reaction notes

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