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

HRID 58125Notes

Reaction equation

HRID 58125 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[NH2:13].Cl[C:15](Cl)([O:17]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCOCC1>[Cl:1][C:2]1[C:3]([N:13]=[C:15]=[O:17])=[C:4]([Cl:12])[C:5]([O:10][CH3:11])=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 594862532,6-Dichloro-3,5-dimethoxyaniline

Product 1

HCID 860869932,6-Dichloro-3,5-dimethoxyphenyl isocyanateYield 162%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2,6-dichloro-3,5-dimethoxy-phenylamine (500 g, 2.25 mmol), triphosgene (335 mg, 1.12 mmol) and TEA (342 g, 3.38 mmol) in dioxane (15 mL) was heated to 130° C. for 2 hours under microwave. The reaction was concentrated and the residue was purified by flash chromatography on silica eluting with DCM to obtain the title compound (450 mg, yield: 80%). 1H-NMR (400 MHz, CDCl3) δ 3.92 (s, 6H), 6.42 (s, 1H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by flash chromatography on silica eluting with DCM

Sources & evidence

ORD record
ord-061b4f02256e4bbcbb85530fcb0c5cc2
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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