Triphosgene → 5-Chloro-3-methyl isatoic anhydride

HRID 2427034Notes

Reaction equation

HRID 2427034 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](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1>[Cl:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:2]2[NH:1][C:14](=[O:16])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 116440442-Amino-5-chloro-3-methylbenzoic acid

Product 1

HCID 115502595-Chloro-3-methyl isatoic anhydrideYield 187%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.85 g of 2-amino-5-chloro-3-methylbenzoic acid, 0.90 g of triphosgene and 10 ml of tetrahydrofuran was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and a precipitated crystal was washed with water to obtain 1.20 g of 6-chloro-8-methyl-1H-benzo[d]-1,3-oxazine-2,4-dione of the formula:

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washa precipitated crystal was washed with water

Sources & evidence

ORD record
ord-d6a62bf8b01a452abd397a94060cf131
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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