Ethyl isocyanate → HCID 21224890, compound

HRID 583203Notes

Reaction equation

HRID 583203 reaction equation
[C:1]1([CH:7]2[CH2:11][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])[C:9](=[O:24])[NH:8]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([CH:7]2[CH2:11][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])[C:9](=[O:24])[NH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 21224873HCID 21224873, compound

Product 1

HCID 21224890HCID 21224890, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

4-Phenyl-1-(indoline-5-sulfonyl)-4,5-dihydro-2-imidazolone (0.25g, 0.73 mmol) prepared in Preparation 5 was dissolved in 10 m of toluene and then ethylisocyanate (0.1 m, 1.09 mmol) was added thereto. The reaction mixture was stirred at 50-60° C. for 18 hours. After the solvent was evaporated, the residue was dissolved in 50 m of dichloromethane, washed twice with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography (eluent: dichloromethane/methanol=15/1, v/v) to afford 0.22 g of the title compound.

Workup

  1. customAfter the solvent was evaporated
  2. dissolutionthe residue was dissolved in 50 m of dichloromethane
  3. washwashed twice with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product thus obtained
  7. customwas purified by silica gel column chromatography (eluent: dichloromethane/methanol=15/1, v/v)

Sources & evidence

ORD record
ord-803d48eda961408bbc1033b251b56807
Source dataset
uspto-grants-1999_07
Patent number
US05929103

Reaction notes

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