Water → HCID 54087098, compound

HRID 2270134Notes

Reaction equation

HRID 2270134 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[CH2:9][S:8][C:7]1=[O:12].[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=O.C(OCC)(=O)C.O>C(O)C.N1CCCCC1>[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=[S:8]1[CH2:9][C:10](=[O:11])[N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:7]1=[O:12]

Participants

7

Reactant 4

HCID 962WaterHCID 69962-ChlorobenzaldehydeHCID 8857Ethyl AcetateHCID 86183559HCID 86183559, compound

Product 1

HCID 54087098HCID 54087098, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A solution of 400 mg of 3-(3-methoxy-n-propyl)-2,4-thiazolidinedione and 260 mg of 2-chlorobenzaldehyde in 4 ml of ethanol with one drop of piperidine was refluxed for 4 hours. The mixture was then worked up with ethyl acetate and water. The crude product was purified on a silica gel column (5 % methanol in dichloromethane) to provide 200 mg of 1-(2-chlorophenylmethylene)-3-(3-methoxy-n-propyl)-2,4-thiazolidinedione. (P15 can also be obtained from Aldrich Chemical.)

Workup

  1. customThe crude product was purified on a silica gel column (5 % methanol in dichloromethane)

Sources & evidence

ORD record
ord-a71588462c4f47f188e569c2fcd2ea47
Source dataset
uspto-grants-2001_12
Patent number
US06331555B1

Reaction notes

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