Phosgene → 2,4,6-Trimethoxyphenyl isocyanate

HRID 1756970Notes

Reaction equation

HRID 1756970 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([O:12][CH3:13])[C:4]=1[NH2:5].[C:14](Cl)(Cl)=[O:15]>C1(C)C=CC=CC=1.CCOCC>[CH3:13][O:12][C:6]1[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=[C:3]([O:2][CH3:1])[C:4]=1[N:5]=[C:14]=[O:15]

Participants

5

Reactant 2

HCID 6371Phosgene2×HCID 842712,4,6-Trimethoxyaniline

Product 1

HCID 100818122,4,6-Trimethoxyphenyl isocyanate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 2,4,6-trimethoxyaniline (71.1 g, 0.324 mol) in a 12.5% wt/wt solution (540 mL) of phosgene in toluene was heated on a steam bath with periodic swirling for 3 hours. Additional phosgene in toluene solution (2×270 mL) was added after 1 and 2 hours. The suspension was allowed to cool, placed under house vacuum, and stirred for 2.5 days. The mixture was rotoevaporated to a dark purple solid. The residue was dissolved in ether (450 mL), filtered, rotoevaporated, and dried in vacuo to give a purple amorphous solid; yield 66.9 g (98.7%), mp 67°-70° C.

Workup

  1. temperaturewas heated on a steam bath
  2. temperatureto cool
  3. filtrationfiltered
  4. customdried in vacuo
  5. customto give a purple amorphous solid

Sources & evidence

ORD record
ord-daa82f64f67c4baeb0c4827807f23470
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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