Phosgene → 1-(Isocyanatomethyl)-4-methylbenzene

HRID 1985213Notes

Reaction equation

HRID 1985213 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[C:10](=O)(O)[O-:11].[Na+].C(Cl)(Cl)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[N:7]([CH2:6][C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][CH:4]=1)=[C:10]=[O:11]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 660354-MethylbenzylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 27333881-(Isocyanatomethyl)-4-methylbenzene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of p-methyl benzylamine (25 g, 0.21 mol) in CH2Cl2 (200 mL) and aqueous saturated solution of sodium bicarbonate (200 mL) was cooled to 0° C. and then treated dropwise with a 20% solution of phosgene in toluene (100 mL). The reaction was stirred at room temperature for 20 minutes and then the organic layer removed and the aqueous layer back-extracted with CH2Cl2. The organic layer was dried (Na2SO4) and the solvent removed in vacuo to give 20.6 g 1-isocyanatomethyl-4-methyl-benzene that was utilized directly in the next reaction without purification.

Workup

  1. customthe organic layer removed
  2. extractionthe aqueous layer back-extracted with CH2Cl2
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1f16e210f6234dfd9ea88b6e972b6904
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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