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

HRID 887325Notes

Reaction equation

HRID 887325 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)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

The product from Example 297A (4.00 g, 19.4 mmol) in acetone (9 mL) at 0° C. was treated with 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 toluene solution was dried over MgSO4, filtered, and the filtrate was heated to reflux for 1 hour. The cooled solution was concentrated under reduced pressure to provide the title compound.

Workup

  1. extractionthe mixture was extracted with toluene (20 mL)
  2. dry with materialThe toluene solution was dried over MgSO4
  3. filtrationfiltered
  4. temperaturethe filtrate was heated
  5. temperatureto reflux for 1 hour
  6. concentrationThe cooled solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-249d3dab003e4b91859cc370b9a24baf
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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