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

HRID 2107554Notes

Reaction equation

HRID 2107554 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-e695006700da4fce81f4571e53272503
Source dataset
uspto-grants-1990_06
Patent number
US04935413

Reaction notes

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