1,1,1,3,3,3-Hexafluoro-2-propanol → Hexafluoroisopropyl beta-chloroisobutyrylcarbamate

HRID 2107555Notes

Reaction equation

HRID 2107555 reaction equation
[Cl:1][CH2:2][CH:3]([CH3:9])[C:4]([N:6]=[C:7]=[O:8])=[O:5].[CH:10]([OH:19])([C:15]([F:18])([F:17])[F:16])[C:11]([F:14])([F:13])[F:12]>C(Cl)(Cl)Cl>[Cl:1][CH2:2][CH:3]([CH3:9])[C:4]([NH:6][C:7](=[O:8])[O:19][CH:10]([C:15]([F:18])([F:17])[F:16])[C:11]([F:14])([F:13])[F:12])=[O:5]

Participants

4

Reactant 2

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 137662253-Chloro-2-methylpropanoyl isocyanate

Product 1

HCID 53764557Hexafluoroisopropyl beta-chloroisobutyrylcarbamate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of beta-chloroisobutyryl isocyanate (7.38 g; 50 mmol) in chloroform (50 ml), a solution of 1,1,1,3,3,3-hexafluoroisopropanol (8.4 g; 50 mmol) in chloroform (10 ml) was dropwise added at 10° C. under ice-cooling. After completion of the addition, the resultant mixture was stirred for 1 hour, whereby hexafluoroisopropyl beta-chloroisobutyrylcarbamate was produced. A solution of triethylamine (5.05 g; 50 mmol) in chloroform (50 ml) was added to the reaction mixture in 30 minutes under ice-cooling. The reaction mixture was stirred for 1 hour, and precipitated triethylamine hydrochloride (6.87 g) was eliminated by filtration. The filtrate was concentrated under reduced pressure to give hexafluoroisopropyl N-methacryloylcarbamate (13.4 g), which was recrystallized from benzene to give colorless prisms. M.P., 112.5°-113° C.

Workup

  1. temperaturecooling
  2. additionAfter completion of the addition

Sources & evidence

ORD record
ord-11fe235d68b6486d951aecddd7401396
Source dataset
uspto-grants-1990_06
Patent number
US04935413

Reaction notes

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