Potassium Iodide → 2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione

HRID 2039680

Reaction equation

HRID 2039680 reaction equation
[OH:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].Cl.Cl[CH2:15][C:16]1[N:17]=[C:18]([NH2:21])[S:19][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C.O>[NH2:21][C:18]1[S:19][CH:20]=[C:16]([CH2:15][O:1][N:2]2[C:10](=[O:11])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]2=[O:12])[N:17]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10665N-HydroxyphthalimideHCID 10796Cesium carbonateHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)

Product 1

HCID 3410772-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dioneYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-hydroxy-1H-isoindole-1,3(2H)-dione (4.13 g, 15.0 mmol) in acetonitrile (150 mL) were added 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (50.1 g, 337 mmol), cesium carbonate (210 g, 643 mmol) and potassium iodide (2.54 g, 15.3 mmol). The heterogenous mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water, the insolubles were filtered off, rinsed with water and dried over night to afford 2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione as a colourless solid [36.0 g, yield 43%; HPLC/MS: m/z=276 (M+H); log P(HCOOH)=0.74].

Workup

  1. filtrationthe insolubles were filtered off
  2. washrinsed with water
  3. customdried over night

Sources & evidence

ORD record
ord-e2ea30608b7442e6bab564d433391754
Source dataset
uspto-grants-2013_11
Patent number
US08580799B2

Linked notes

Loading…