Hantzsch ester → HCID 21705002, compound

HRID 1595505Notes

Reaction equation

HRID 1595505 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][O:22][C:23]3[CH:36]=[CH:35][C:26]([CH:27]=[C:28]4[S:32][C:31](=[O:33])[NH:30][C:29]4=[O:34])=[CH:25][CH:24]=3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(OC(C1CC(C(OCC)=O)=C(C)NC=1C)=O)C>>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][O:22][C:23]3[CH:36]=[CH:35][C:26]([CH2:27][CH:28]4[S:32][C:31](=[O:33])[NH:30][C:29]4=[O:34])=[CH:25][CH:24]=3)=[CH:16][CH:15]=2)(=[O:11])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 70849Hantzsch esterHCID 54551481HCID 54551481, compound

Product 1

HCID 21705002HCID 21705002, compoundYield 41.2%

Conditions

Temperature
145 °C

Procedure

2,4 g (4.6 mmole) 5-(4-[2-(4-(3-nitrophenylsulfonyloxy)phenyl)ethoxy]benzylidene)thiazolidine-2,4-dione and 3.5 g (14 mmole) diethyl-1,4-dihydro-2,6-dimethyl-3,5-pyridine dicarboxylate were mixed and heated to 145° C. under vacuum and after 1-2 hours the heat was removed. The solid material was dissolved in toluene, evaporated in vacuo and purified by chromatography on silica gel twice with ethyl acetate:petroleum ether (1:1) as eluents to give 1.002 g (yield 41%) of the desired product.

Workup

  1. customwas removed
  2. dissolutionThe solid material was dissolved in toluene
  3. customevaporated in vacuo
  4. custompurified by chromatography on silica gel twice with ethyl acetate:petroleum ether (1:1) as eluents

Sources & evidence

ORD record
ord-c563403f0c904a45a328d468fcc0025f
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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