Ethyl isocyanate → HCID 20231712, compound

HRID 2290173Notes

Reaction equation

HRID 2290173 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[NH:13][C:14]([CH:19]([CH3:21])[CH3:20])([CH3:18])[C:15](=[O:17])[N:16]=1)=[O:5])[CH3:2].[CH2:22]([N:24]=[C:25]=[O:26])[CH3:23].C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:13]([C:25](=[O:26])[NH:24][CH2:22][CH3:23])[C:14]([CH:19]([CH3:20])[CH3:21])([CH3:18])[C:15](=[O:17])[N:16]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178468792HCID 178468792, compound

Product 1

HCID 20231712HCID 20231712, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9 g (0.031 mole) of 2-(2-ethoxycarbonylphenyl)-5-isopropyl-5-methyl-4-oxo-2-imidazoline are dissolved in 30 ml of absolute methylene chloride, and 2.7 g (0.038 mole) of ethyl isocyanate and 0.5 ml of DBU are added at room temperature. After a reaction time of 1 hour, the mixture is poured onto ice and the organic phase is washed twice with water, dried and evaporated. 11.0 g (98% of theory) of 2-(2-ethoxycarbonylphenyl)-1-N-ethylcarbamoyl-5-isopropyl-5-methyl-4-oxo-2-imidazoline are obtained as colorless tablets of melting point 85°-87° C.

Workup

  1. additionAfter a reaction time of 1 hour, the mixture is poured onto ice
  2. washthe organic phase is washed twice with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-2b163768fec141eda9858b737ac6166a
Source dataset
uspto-grants-1986_10
Patent number
US04615726

Reaction notes

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