Isopropyl isocyanate → HCID 22170124, compound

HRID 1822744Notes

Reaction equation

HRID 1822744 reaction equation
[CH3:1][C:2]([CH:6]1[CH:15]2[CH2:16][CH:17]=[CH:18][CH:14]2[C:13]2[CH:12]=[C:11]([N+:19]([O-:21])=[O:20])[CH:10]=[CH:9][C:8]=2[NH:7]1)([CH3:5])[CH2:3][NH2:4].[CH:22]([N:25]=[C:26]=[O:27])([CH3:24])[CH3:23]>CN(C)C=O.O.C(OCC)(=O)C>[CH:22]([NH:25][C:26]([NH:4][CH2:3][C:2]([CH3:1])([CH:6]1[CH:15]2[CH2:16][CH:17]=[CH:18][CH:14]2[C:13]2[CH:12]=[C:11]([N+:19]([O-:21])=[O:20])[CH:10]=[CH:9][C:8]=2[NH:7]1)[CH3:5])=[O:27])([CH3:24])[CH3:23]

Participants

6

Reactant 2

HCID 61277Isopropyl isocyanateHCID 22170125HCID 22170125, compound

Product 1

HCID 22170124HCID 22170124, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound of Example 49 (57 mg) was dissolved in 2 ml of dimethylformamide, and 0.03 ml of isopropyl isocyanate was added. After 30 minutes stirring at room temperature, the reaction mixture was diluted with water and ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=1:1) to obtain 62 mg of the captioned compound. Its physical properties are shown below.

Workup

  1. washThe ethyl acetate layer was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-8c6a30cb5a1f4ba4ba97ba3a57fdc979
Source dataset
uspto-grants-2006_05
Patent number
US07037919B1

Reaction notes

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