Ethyl isocyanate → HCID 21224892, compound

HRID 1584660Notes

Reaction equation

HRID 1584660 reaction equation
[C:1]1([C:7]2[NH:8][C:9](=[O:24])[N:10]([S:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[NH:20][CH2:19][CH2:18]4)(=[O:14])=[O:13])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:25]([N:27]=[C:28]=[O:29])[CH3:26]>C1(C)C=CC=CC=1>[C:1]1([C:7]2[NH:8][C:9](=[O:24])[N:10]([S:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([C:28](=[O:29])[NH:27][CH2:25][CH3:26])[CH2:19][CH2:18]4)(=[O:14])=[O:13])[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 11002343HCID 11002343, compound

Product 1

HCID 21224892HCID 21224892, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

4-Phenyl-1-(indoline-5-sulfonyl)-2-imidazolone (100 mg, 0.29 mmol) prepared in Preparation 3 was dissolved in 10 ml of toluene, and ethylisocyanate (35 μl, 0.435 mmol) was added thereto. The reaction mixture was stirred for 8 hours at 80° C. The solvent was evaporated therefrom under reduced pressure. The residue was dissolved in 30 ml of dichloromethane, washed twice with brine, dried over anhydrous magnesium sulfate, concentrated to an oily state, and then purified by silica gel column chromatography (eluent:dichloromethane/methanol=15/1, v/v) to obtain 113 mg of the title compound.

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in 30 ml of dichloromethane
  3. washwashed twice with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to an oily state
  6. custompurified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-f4873f004b5d453a80facc56797fddb0
Source dataset
uspto-grants-1999_08
Patent number
US05932742

Reaction notes

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