tert-Butanol → tert-Butyl (3-chloropropanoyl)carbamate

HRID 1707516Notes

Reaction equation

HRID 1707516 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([N:6]=[C:7]=[O:8])=[O:5].[C:9]([OH:13])([CH3:12])([CH3:11])[CH3:10]>ClC(Cl)C>[Cl:1][CH2:2][CH2:3][C:4]([NH:6][C:7](=[O:8])[O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:5]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 135723743-Chloropropanoyl isocyanate

Product 1

HCID 14221823tert-Butyl (3-chloropropanoyl)carbamate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To beta-chloropropionyl isocyanate (13.3 g; 100 mmol) in dichloroethane (20 g), a solution of t-butanol (7.4 g; 100 mmol) in dichloroethane (20 g) was dropwise added under ice-cooling in 5 minutes, whereby t-butyl beta-chloropropionylcarbamate was produced. Triethylamine (9.8 g; 100 mmol) was added to the reaction mixture, and the resultant mixture was stirred for 60 minutes. Precipitated salts were eliminated by filtration, and the filtrate was concentrated under reduced pressure to give t-butyl acryloylcarbamate as crude crystals, which were recrystallized from chloroform to give colorless needles. M.P., 131°-132° C.

Workup

  1. temperaturecooling in 5 minutes

Sources & evidence

ORD record
ord-1a2906bab4e7477eb5c1aa0aa62f1bd8
Source dataset
uspto-grants-1994_10
Patent number
US05354495

Reaction notes

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