Diphosgene → Benzene, 2-isocyanato-1-methoxy-4-(trifluoromethyl)-
Reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:4]=1[NH2:5].CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.Cl[C:31](OC(Cl)(Cl)Cl)=[O:32]>ClCCl>[N:5]([C:4]1[CH:6]=[C:7]([C:10]([F:11])([F:12])[F:13])[CH:8]=[CH:9][C:3]=1[O:2][CH3:1])=[C:31]=[O:32]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3 g (15.69 mmol) of 2-methoxy-5-trifluoromethylaniline are dissolved in 100 ml of dichloromethane, and 6.73 g (31.39 mmol) of 1,8-bis(dimethylamino)naphthalene are added. At 0-5° C., 2.24 g (11.3 mmol) of trichloromethyl chloroformate, dissolved in 50 ml of dichloromethane, are added dropwise, and the mixture is stirred at 0° C. for 30 min and at room temperature for 60 min. At 0° C., the mixture is washed with 1N hydrochloric acid, ice-water and sodium bicarbonate solution. Drying over magnesium sulphate and removal of the solvent by distillation gives the product. The isocyanate is then used in the subsequent reactions without further purification.
Workup
- additionare added dropwise
- washAt 0° C., the mixture is washed with 1N hydrochloric acid, ice-water and sodium bicarbonate solution
- dry with materialDrying over magnesium sulphate and removal of the solvent by distillation
- customgives the product
- customThe isocyanate is then used in the subsequent reactions without further purification
Sources & evidence
- ORD record
- ord-80870061d6354dc8b2c15113d16bf261
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07960387B2
Reaction notes
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