4-Methylmorpholine → 1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene
Reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.CN1CCOCC1.[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=1[C:28]([F:31])([F:30])[F:29]>C(Cl)(Cl)Cl>[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([N:25]=[C:2]=[O:4])=[CH:23][C:22]=1[C:28]([F:29])([F:30])[F:31]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
With a waste gas absorption device, triphosgen (167 g, 0.56 mol, 0.5 eq) was dissolved in chloroform (500 mL). A solution of N-methyl morpholine (11.4 g, 0.11 mol, 0.1 eq) in chlorofrom (100 mL) was added dropwise into the above mixture at 5° C. After addition, a solution of 4-chloro-3-(trifluoromethyl)aniline (220 g, 1.13 mol, 1.0 eq) in chloroform (700 mL) was added dropwise at 10° C. The mixture was warmed to 40° C. and stirred for 15 hours, and then warmed to 50° C. and stirred for 5 hours, and then heated to 60-65° C. and refluxed for 5 hours. The solvent was removed under atmospheric pressure. The residue was distilled under vacumm (oil temperature 110-120° C., vacuum 200 Pa) and the fractions at 95-100° C. were collected to give the title compound (200 g, purity 98.7%, yield 84%) as a colorless liquid.
Workup
- additionAfter addition
- temperaturewarmed to 50° C.
- stirringstirred for 5 hours
- temperatureheated to 60-65° C.
- temperaturerefluxed for 5 hours
- customThe solvent was removed under atmospheric pressure
- distillationThe residue was distilled under vacumm (oil temperature 110-120° C., vacuum 200 Pa)
- customthe fractions at 95-100° C. were collected
Sources & evidence
- ORD record
- ord-a6eb5dcb61b74fe98448290570bf5cd5
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669369B2
Reaction notes
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