Carbamic acid, ethyl ester → HCID 178517462, compound

HRID 1975818Notes

Reaction equation

HRID 1975818 reaction equation
[NH2-:1].[Na+].C1C=C[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[C:28](#[N:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.ClC(OCC)=O.[NH2:42][C:43]([O:45]CC)=O>C(O)C>[OH:45][C:43]1[N:42]=[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:35]=[C:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:1]=1

Participants

7

Reactant 5

HCID 5641Carbamic acid, ethyl esterHCID 7505BenzonitrileHCID 10928Ethyl chloroformateHCID 24533Sodium amideHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)2×

Product 1

HCID 178517462HCID 178517462, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

100 g (2.4 mol) of sodium amide (95%) are stirred for 12 hours at room temperature in 500 ml of ®Dowtherm (mixture of 26.5% by weight of diphenyl and 73.5% by weight of diphenyl ether) in the presence of glass beads. The glass beads are then separated and washed with 500 ml of ®Dowtherm. The resultant suspension is heated to 90° C. and 232 g (2.35 mol) of benzonitrile are added dropwise over 1 hour such that the temperature does not rise above 105° C. Sniffing is continued for 3 hours at 95° C., then the reaction mixture is cooled to 15° C. and 260.4 g (2.4 mol) of ethyl chloroformate are added dropwise over 2 hours. The reaction mixture is then heated to 170° C. and the pressure is lowered to 150-80 mbar, whereupon 300 g of distillate consisting of ethanol, urethane and ®Dowtherm are distilled over. After a reaction time of 2 hours, the batch is cooled, filtered, and the filter residue is washed with 1 liter of methanol, giving 255.4 g of a white product of formula ##STR3##

Workup

  1. customThe glass beads are then separated
  2. washwashed with 500 ml of ®Dowtherm
  3. customdoes not rise above 105° C
  4. temperaturethe reaction mixture is cooled to 15° C.
  5. temperatureThe reaction mixture is then heated to 170° C.
  6. distillationare distilled over
  7. temperatureAfter a reaction time of 2 hours, the batch is cooled
  8. filtrationfiltered
  9. washthe filter residue is washed with 1 liter of methanol

Sources & evidence

ORD record
ord-ac471942dfd847c0908c9222342730d3
Source dataset
uspto-grants-1994_02
Patent number
US05288868

Reaction notes

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