Water → 4-Chloroisatoic anhydride

HRID 482309

Reaction equation

HRID 482309 reaction equation
[Cl-].C([N+]1C=CC=CC=1)CCCCCCCCCCC.O.[C:21](Cl)(Cl)=[O:22].[Cl:25][C:26]1[CH:27]=[C:28]([NH2:35])[C:29](=[CH:33][CH:34]=1)[C:30]([OH:32])=[O:31]>C1(C)C=CC=CC=1>[CH:34]1[C:26]([Cl:25])=[CH:27][C:28]2[NH:35][C:21]([O:31][C:30](=[O:32])[C:29]=2[CH:33]=1)=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6371PhosgeneHCID 7717Dodecylpyridinium chlorideHCID 666462-Amino-4-chlorobenzoic acid

Product 1

HCID 3291054-Chloroisatoic anhydrideYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

According to the same manner as in Example 4, except that the flask was changed to 300 ml flask, laurylpyridinium chloride was not used, 103 g of water was added, and that amounts of toluene, phosgene and 4-chloroanthranilic acid were changed to 34 g, 40 g and 35 g, respectively, 35.6 g of 7-chloroisatoic anhydride (purity: 73.8%) was obtained. The yield was 67% and the volume efficiency was 9 g/100 ml.

Workup

  1. customwas changed to 300 ml flask

Sources & evidence

ORD record
ord-cc6f524ba1f14846bd4f24da62559d0f
Source dataset
uspto-grants-1998_08
Patent number
US05795984

Linked notes

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