Hydroxyacetate → HCID 13080193, compound

HRID 1193558Notes

Reaction equation

HRID 1193558 reaction equation
C([O-])(=O)CO.[Cl:6][C:7]1[CH:8]=[C:9]([NH:14][C:15]([O:17][CH2:18][C:19]([O-:21])=O)=[O:16])[CH:10]=[C:11]([Cl:13])[CH:12]=1.ClC1C=C(N(C(NC2C=C(Cl)C=C(Cl)C=2)=O)C([O-])=O)C=C(Cl)C=1>>[Cl:6][C:7]1[CH:8]=[C:9]([N:14]2[C:19](=[O:21])[CH2:18][O:17][C:15]2=[O:16])[CH:10]=[C:11]([Cl:13])[CH:12]=1

Participants

4

Reactant 3

HCID 5460308HydroxyacetateHCID 21272614HCID 21272614, compound2×HCID 86742787HCID 86742787, compound2×

Product 1

HCID 13080193HCID 13080193, compoundYield 90%

Procedure

The conventional reaction of equimolar amounts of 3,5-DCI and a glycolate gives a mixture of 85-90% of an N-(3,5-dichlorophenyl)-carbamyloxyacetate (I) and 10-15% of an N,N'-bis-(3,5-dichlorophenyl)-allophanate (II), the percentages being based on 3,5-DCI employed. Both the N-(3,5-dichlorophenyl)-carbamyloxyacetate and the N,N'-bis-(3,5-dichlorophenyl)-allophanate undergo cyclization in the presence of a basic catalyst to give an N-(3,5-dichlorophenyl)-oxazolidine-2,4-dione (III), this product being obtained in a yield of about 90%, based on 3,5-DCI employed, in the case of the above mixture.

Workup

  1. customgives

Sources & evidence

ORD record
ord-3ff6dd084b4a4366b9b8a663ddc39436
Source dataset
uspto-grants-1989_03
Patent number
US04810799

Reaction notes

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