Ethyl Acetate → Carbamic acid, ethyl ester

HRID 1828007Notes

Reaction equation

HRID 1828007 reaction equation
[C:1]([C:11]([NH:13][CH2:14][CH2:15][OH:16])=[O:12])([C:4]([C:7]([F:10])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].[C:17]([O:20][CH2:21][CH3:22])(=[O:19])C>O>[C:1]([C:11]([NH:13][CH2:14][CH2:15][OH:16])=[O:12])([C:4]([C:7]([F:10])([F:8])[F:9])([F:6])[F:5])([F:3])[F:2].[NH2:13][C:17]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 4613030N-(2-Hydroxyethyl)perfluorobutanamide

Product 2

HCID 5641Carbamic acid, ethyl esterHCID 4613030N-(2-Hydroxyethyl)perfluorobutanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A 500 mL round bottom flask equipped with a magnetic stirrer and fitted with a condenser was charged with C3F7CONHC2H4OH (30.0 grams), ethyl acetate (53.0 grams) and N3300 (22.6 grams). Upon dissolution, the mixture was heated to 80° C., DBTDL (one drop) was added, and heating was continued for 16 hours. The reaction was monitored by FTIR analysis, which showed the disappearance of the —NCO band at approximately 2289 wavenumbers. A solution of Witconate DS-10 (2.6 grams) in DI water (200.0 grams) was slowly added to the solution in the 500 mL flask with vigorous stirring, keeping the temperature between 65° C. and 73° C. during addition. Upon completion of addition, the solution was sonicated with a Cole-Parmer ultrasonic homogenizer (model CPX 600, available from Cole-Parmer, Vernon Hills, Ill.) for 8 minutes. The ethyl acetate was removed using a rotary evaporator, yielding C3F7CONHC2H4OH/N3300 Urethane.

Workup

  1. customA 500 mL round bottom flask equipped with a magnetic stirrer
  2. customfitted with a condenser
  3. dissolutionUpon dissolution
  4. additionDBTDL (one drop) was added
  5. temperatureheating
  6. customthe temperature between 65° C. and 73° C.
  7. additionduring addition
  8. additionUpon completion of addition
  9. customthe solution was sonicated with a Cole-Parmer ultrasonic homogenizer (model CPX 600, available from Cole-Parmer, Vernon Hills, Ill.) for 8 minutes
  10. customThe ethyl acetate was removed
  11. customa rotary evaporator

Sources & evidence

ORD record
ord-d64359a0973147c29097443cca8e880e
Source dataset
uspto-grants-2006_06
Patent number
US07056846B2

Reaction notes

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