Sodium Carbonate → 1-{3-[(1,3-Benzothiazol-2-yl)methoxy]phenyl}pyrrolidine-2,5-dione

HRID 465135

Reaction equation

HRID 465135 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:16])[CH2:10][CH2:11][C:12](OC)=[O:13])[CH:5]=[CH:6][CH:7]=1.Cl[CH2:18][C:19]1[S:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[Na+].[Na+]>[I-].[K+].CC(C)=O>[S:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[CH2:18][O:1][C:2]1[CH:3]=[C:4]([N:8]2[C:9](=[O:16])[CH2:10][CH2:11][C:12]2=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 3049782-(Chloromethyl)benzothiazoleHCID 13491817Methyl 4-(3-hydroxyanilino)-4-oxobutanoate

Product 1

HCID 134918181-{3-[(1,3-Benzothiazol-2-yl)methoxy]phenyl}pyrrolidine-2,5-dioneYield 60.9%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 4-[[3-(hydroxy)phenyl]amino]-4-oxobutanoic acid, methyl ester (1.45 g, 6.5 mmol), 2-chloromethylbenzothiazole (1.20 g, 6.5 mmol), cesium carbonate (1.0 g), sodium carbonate (0.7 g), potassium iodide (5 mg) and acetone (60 ml) is heated at reflux for 2 hours. The reaction is filtered through a pad of Celite and silica gel and the solvent is removed in vacuo. Recrystallization from acetone gives 1.34 g (56% yield) of product, m.p. 175°-176° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe reaction is filtered through a pad of Celite and silica gel
  4. customthe solvent is removed in vacuo
  5. customRecrystallization from acetone

Sources & evidence

ORD record
ord-344a4a7e534e487d9fdbceb644f876a5
Source dataset
uspto-grants-1985_10
Patent number
US04550172

Linked notes

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