Ethyl isocyanate → HCID 21224892, compound

HRID 583199Notes

Reaction equation

HRID 583199 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 m of toluene, and ethylisocyanate (35 μ, 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 m 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. additionwas added
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in 30 m of dichloromethane
  4. washwashed twice with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated to an oily state
  7. custompurified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-caaa5244834f468c855b0bbb10fc38cb
Source dataset
uspto-grants-1999_07
Patent number
US05929103

Reaction notes

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