Phosgene → 5-Isocyanato-1,2,3-trimethoxybenzene

HRID 1768563Notes

Reaction equation

HRID 1768563 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[NH2:6].[C:14](Cl)(Cl)=[O:15]>C1(C)C=CC=CC=1>[CH3:13][O:12][C:8]1[CH:7]=[C:5]([N:6]=[C:14]=[O:15])[CH:4]=[C:3]([O:2][CH3:1])[C:9]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 322853,4,5-Trimethoxyaniline

Product 1

HCID 5177665-Isocyanato-1,2,3-trimethoxybenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3,4,5-trimethoxyaniline (365 mg; 2.0 mmol) in toluene (20 ml) and phosgene (6 ml 20% in toluene; 12 mmol) was refluxed for 6 h. The solvent was removed under reduced pressure to give crude 3,4,5-trimethoxyphenylisocyanate. To the crude product was added 3(4-(6-fluoro-1,2-benzisoxazol-3-yl)-piperidine) propanol (420 mg; 1.5 mmol) in DMF (10 ml). The mixture was stirred at 100° C. for 2 h and then at room temperature for 16 h, whereupon it was taken up in ethyl acetate and water. The organic phase was washed with water and saturated sodium chloride and concentrated in vacuo. The resulting oil was taken up in acetone/ethanol (4:1, v/v) and oxalic acid (150 mg) in 2 ml acetone added to precipitate the desired product. The product was washed with ice cold ethanol giving 550 mg of the title compound. M.p. 77°-80° C. MS (70 eV): m/z 487 (9%, M+), 287 (31), 233 (40), 209 (56), 194 (45), 140 (67), 96 (100).

Workup

  1. temperaturewas refluxed for 6 h
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4518564fa251482ca33c1b294deaeda9
Source dataset
uspto-grants-1995_01
Patent number
US05378714

Reaction notes

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