Acetone → 1-Chloro-4-(2-isocyanatopropan-2-yl)benzene

HRID 887210Notes

Reaction equation

HRID 887210 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])C(Cl)=O)=[CH:4][CH:3]=1.[N-:14]=[N+]=[N-].[Na+].C[C:19](C)=[O:20]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:14]=[C:19]=[O:20])([CH3:12])[CH3:13])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 33557Sodium AzideHCID 135368632-(4-Chlorophenyl)-2-methylpropanoyl chloride

Product 1

HCID 131183231-Chloro-4-(2-isocyanatopropan-2-yl)benzeneYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

The product of Example 76A (4.00 g, 19.4 mmol) in acetone (9 mL) at 0° C. was treated with a solution of sodium azide (1.27 g) in water (9 mL) dropwise over 15 minutes. After stirring for 30 minutes at 0° C., the mixture was extracted with toluene (20 mL). The organic extract was dried with MgSO4, filtered, and the filtrate heated at reflux for 1 hour. The mixture was allowed to cool to room temperature and was concentrated under reduced pressure to provide the title compound as a pale yellow oil (3.45 g, 96%).

Workup

  1. extractionthe mixture was extracted with toluene (20 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried with MgSO4
  4. filtrationfiltered
  5. temperaturethe filtrate heated
  6. temperatureat reflux for 1 hour
  7. temperatureto cool to room temperature
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-b92d54e54f8e44d6b7766c96c5f6410d
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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