Phosgene → 2,4,6-Trimethoxyphenyl isocyanate

HRID 1756977Notes

Reaction equation

HRID 1756977 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:5]=1[NH2:6].[C:15](Cl)(Cl)=[O:16]>C1(C)C=CC=CC=1>[CH3:14][O:13][C:7]1[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=[C:4]([O:3][CH3:2])[C:5]=1[N:6]=[C:15]=[O:16]

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 27644342,4,6-trimethoxyaniline Hydrochloride

Product 1

HCID 100818122,4,6-Trimethoxyphenyl isocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

A suspension of 2,4,6-trimethoxyaniline hydrochloride (71.1 g, 0.324 mol) in a 12.5% wt/wt solution (540 mL) of phosgene in toluene was heated (95° C.) for 3 hours. Additional phosgene solution (2×270 mL) was added every hour. The mixture was allowed to cool and stirred under house vacuum for 2 days. The mixture was rotoevaporated to a solid. The solid was triturated with ether (450 mL), filtered, and the filtrate rotoevaporated to give a purple amorphous solid; yield 66.9 g (99%); mp 67°-70° C.

Workup

  1. temperatureto cool
  2. customThe solid was triturated with ether (450 mL)
  3. filtrationfiltered
  4. customto give a purple amorphous solid

Sources & evidence

ORD record
ord-63096adb92024c8080ec14a21e0e1689
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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