4,5-Dichlorophthalic anhydride → 4,5-Dichloro-N-[3-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-phenyl]-phthalamic acid

HRID 1058664Notes

Reaction equation

HRID 1058664 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH:5]=[C:6]1[S:10][C:9](=[O:11])[NH:8][C:7]1=[O:12].[Cl:16][C:17]1[CH:18]=[C:19]2[C:24](=[O:25])[O:23][C:21](=[O:22])[C:20]2=[CH:26][C:27]=1[Cl:28]>C1COCC1.CN(C1C=CN=CC=1)C>[Cl:16][C:17]1[CH:18]=[C:19]([C:24]([NH:1][C:2]2[CH:15]=[CH:14][CH:13]=[C:4]([CH:5]=[C:6]3[S:10][C:9](=[O:11])[NH:8][C:7]3=[O:12])[CH:3]=2)=[O:25])[C:20](=[CH:26][C:27]=1[Cl:28])[C:21]([OH:23])=[O:22]

Participants

5

Reactant 2

HCID 703344,5-Dichlorophthalic anhydrideHCID 734557665-(3-Amino-benzylidene)-thiazolidine-2,4-dione

Product 1

HCID 724977144,5-Dichloro-N-[3-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-phenyl]-phthalamic acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-(3-Amino-benzylidene)-thiazolidine-2,4-dione was dissolved in THF and treated with a solution of 4,5-dichlorophthalic anhydride and a catalytic amount of DMAP. The solution was stirred for 8 hours, then filtered and concentrated under vacuum. The residue was dissolved in EtOAc and washed with water. The organic layer was concentrated to an oil and triturated with hexane to give the product as a solid which was collected by filtration.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water
  5. concentrationThe organic layer was concentrated to an oil
  6. customtriturated with hexane

Sources & evidence

ORD record
ord-b43b34d02d674f21b4281afe2fa4517c
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Reaction notes

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