Diphosgene → 5-Chloro-3-methyl isatoic anhydride

HRID 642600Notes

Reaction equation

HRID 642600 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:14](OC(Cl)(Cl)Cl)=[O:15]>O1CCOCC1>[Cl:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:2]2[NH:1][C:14](=[O:15])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 116440442-Amino-5-chloro-3-methylbenzoic acid2×

Product 1

HCID 115502595-Chloro-3-methyl isatoic anhydride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
42 °C

Procedure

To a suspension of 2-amino-3-methyl-5-chlorobenzoic acid (i.e. product of Example 6, Step A) (97 g, 520 mmol) stirred in dry dioxane (750 mL) at room temperature, trichloromethyl chloroformate (63 g, 320 mmol) was added dropwise. The reaction mixture exothermically warmed slowly to 42° C., and the solid almost completely dissolved before a thick suspension formed again. After the suspension was stirred at ambient temperature for 2.5 hours, the title compound was isolated by filtration, washed with ethyl ether, and dried to yield the title product compound, obtained as a white solid (98g).

Workup

  1. dissolutionthe solid almost completely dissolved before a thick suspension
  2. customformed again

Sources & evidence

ORD record
ord-812e0fc8e4dd4e298a7442bffc8cda12
Source dataset
uspto-grants-2010_04
Patent number
US07696233B2

Reaction notes

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