Ethyl isocyanate → HCID 21393476, compound

HRID 1415470Notes

Reaction equation

HRID 1415470 reaction equation
[CH:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:12]([N:14]=[C:15]=[O:16])[CH3:13]>CCOCC>[CH2:12]([NH:14][C:15]([NH:11][CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)=[O:16])[CH3:13]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 180661,2,3,4-Tetrahydro-1-naphthylamine

Product 1

HCID 21393476HCID 21393476, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution containing 7.4 grams (0.05 mole) of 1,2,3,4-tetrahydro-1-naphthylamine in 150 ml. anhydrous ether is added dropwise with stirring 3.6 grams (0.05 mole) ethyl isocyanate in 10 ml. ether. After the addition, the mixture is heated under reflux for 3 hours, the mixture cooled, and the solid collected by filtration. Recrystallization of the crude product from aqueous methanol gives analytically pure 1-ethyl-3-(1,2,3,4-tetrahydro-1-naphthyl)urea, melting point 178° to 179° C. Other aprotic solvents such as acetone; tetrahydrofuran and benzene may be used as solvents for this reaction. Temperatures employed for the reaction are in the range of 0° to 100° C.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 3 hours
  4. temperaturethe mixture cooled
  5. filtrationthe solid collected by filtration
  6. customRecrystallization of the crude product from aqueous methanol

Sources & evidence

ORD record
ord-19207394bcd04745b9ee0e16dcee5bc1
Source dataset
uspto-grants-1977_01
Patent number
US04005140

Reaction notes

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