Dimethylformamide → 5-[4-{2-[5-(N-Methyl-N-phenylaminomethyl)-2-oxooxazolidin-3-yl]propoxy}benzyl]thiazolidine-2,4-dione

HRID 2294290Notes

Reaction equation

HRID 2294290 reaction equation
[CH3:1][N:2]([CH2:9][CH:10]([OH:31])[CH2:11][NH:12][CH:13]([CH3:30])[CH2:14][O:15][C:16]1[CH:29]=[CH:28][C:19]([CH2:20][CH:21]2[S:25][C:24](=[O:26])[NH:23][C:22]2=[O:27])=[CH:18][CH:17]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CN(C)[CH:34]=[O:35]>>[CH3:1][N:2]([CH2:9][CH:10]1[O:31][C:34](=[O:35])[N:12]([CH:13]([CH3:30])[CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:20][CH:21]3[S:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])=[CH:28][CH:29]=2)[CH2:11]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 214747085-[4-{2-[3-(N-Methyl-N-phenylamino)-2-hydroxypropylamino]propoxy}benzyl]thiazolidine-2,4-dione

Product 1

HCID 214747845-[4-{2-[5-(N-Methyl-N-phenylaminomethyl)-2-oxooxazolidin-3-yl]propoxy}benzyl]thiazolidine-2,4-dione

Procedure

A procedure similar to that described in Example 4 was repeated, except that 0.9 g of 5-[4-{2-[3-(N-methyl-N-phenylamino)-2-hydroxypropylamino]propoxy}-benzyl]thiazolidine-2,4-dione (prepared as described in Example 39), 0.36 g of N,N'-carbonyldiimidazole and 20 ml of anhydrous dimethylformamide were used, to give 0.6 g of the title compound having an Rf value of 0.24 (on silica gel thin layer chromatography, using a 1:1 by volume mixture of ethyl acetate and hexane as the developing solvent).

Sources & evidence

ORD record
ord-c0b37eef3ca845f2a9d795464711d268
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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