Phosgene → 2,6-Dichloro-3,5-dimethoxyphenyl isocyanate

HRID 1038743Notes

Reaction equation

HRID 1038743 reaction equation
[Cl:1][C:2]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([O:11][CH3:12])=[C:5]([Cl:13])[C:3]=1[NH2:4].[C:14](Cl)(Cl)=[O:15]>O1CCOCC1>[Cl:1][C:2]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([O:11][CH3:12])=[C:5]([Cl:13])[C:3]=1[N:4]=[C:14]=[O:15]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 594862532,6-Dichloro-3,5-dimethoxyaniline

Product 1

HCID 860869932,6-Dichloro-3,5-dimethoxyphenyl isocyanate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2,6-dichloro-3,5-dimethoxy-aniline (133 mg, 0.60 mmol; Preparation 2) in 2 ml of dioxane under a nitrogen atmosphere, phosgene (0.54 ml 20% in toluene, 1.0 mmol) is added. The mixture is stirred for 60 min at 100° C., cooled to RT and concentrated in vacuo, yielding 2,6-dichloro-3,5-dimethoxyphenylisocyanate.

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-992c1632b1ef4fa7a31ab59facac0259
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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