Potassium Carbonate → HCID 10130649, compound

HRID 1681156Notes

Reaction equation

HRID 1681156 reaction equation
[S:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[K+].Br[CH2:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[C:22]#[N:23]>C(C(C)=O)C(C)C.O>[C:22]([C:21]1[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=1[CH2:19][N:3]1[CH2:4][CH2:5][S:1][C:2]1=[O:6])#[N:23]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 895992-(Bromomethyl)benzonitrileHCID 974312-ThiazolidinoneHCID 516893Potassium Bicarbonate

Product 1

HCID 10130649HCID 10130649, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture containing 3.09 g (0.03 mol) of 2-thiazolidinone, 11.2 g (0.081 mol) of potassium carbonate, 1.8 g (0.018 mol) of potassium hydrogen carbonate, 0.5 ml (0.027 mol) of water and 6.47 g (0.033 mol) of 2-bromomethylbenzonitrile in 30 ml of methyl isobutyl ketone is refluxed for 5 hours, then cooled down. After adding 30 ml of water the mixture is stirred for 30 minutes, the insoluble precipitate is filtered off, washed twice with 10 ml of water each and dried. After recrystallizing 4.71 g of crude product from 20 ml of ethanol under simultaneous clarification with activated carbon 3.39 g (51.8%) of white, crystalline title compound are obtained, m.p.: 116°-117° C.

Workup

  1. temperatureis refluxed for 5 hours
  2. temperaturecooled down
  3. filtrationthe insoluble precipitate is filtered off
  4. washwashed twice with 10 ml of water each and
  5. customdried
  6. customAfter recrystallizing 4.71 g of crude product from 20 ml of ethanol under simultaneous clarification with activated carbon 3.39 g (51.8%) of white, crystalline title compound
  7. customare obtained

Sources & evidence

ORD record
ord-7f0fd72d39794fc0b5cd9e78333a6b10
Source dataset
uspto-grants-1992_12
Patent number
US05169859

Reaction notes

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