2-Chloro-5-chloromethylthiazole → 2-[(2-Chloro-1,3-thiazol-5-yl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 1646674Notes

Reaction equation

HRID 1646674 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[Cl:13][C:14]1[S:15][C:16]([CH2:19]Cl)=[CH:17][N:18]=1>CN(C=O)C>[Cl:13][C:14]1[S:15][C:16]([CH2:19][N:5]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])=[CH:17][N:18]=1

Participants

4

Reactant 2

HCID 27631792-Chloro-5-chloromethylthiazoleHCID 24194345Phthalimide potassium salt

Product 1

HCID 14816612-[(2-Chloro-1,3-thiazol-5-yl)methyl]-1H-isoindole-1,3(2H)-dioneYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of potassium phthalimide (10.4 g) and dry DMF (100 ml) was dropwise added a solution of 2-chloro-5-(chloromethyl)thiazole (9.0 g) obtained in the same manner as in Example 2, in 10 ml of DMF in an oil bath at 20° C. over 15 min. After completion of the addition stirring was continued at 60° C. for 45 min. followed by separation of insoluble materials by filtration on celite. The filtrate was concentrated under reduced pressure. To the residue was added 100 ml of dichloromethane again followed by separation of insoluble materials by filtration and concentration of the filtrate. The residue was purified by column chromatography (eluted with dichloromethane-ethyl acetate 20:1) to give 12.0 g of N-(2-chloro-5-thiazolylmethyl)phthalimide, mp 108°-109° C.

Workup

  1. additionAfter completion of the addition
  2. customfollowed by separation of insoluble materials by filtration on celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionTo the residue was added 100 ml of dichloromethane
  5. customagain followed by separation of insoluble materials by filtration and concentration of the filtrate
  6. customThe residue was purified by column chromatography (eluted with dichloromethane-ethyl acetate 20:1)

Sources & evidence

ORD record
ord-9923c2a6f828421ca3dcee6a32a3657d
Source dataset
uspto-grants-1993_01
Patent number
US05180833

Reaction notes

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