Methanol → HCID 11476502, compound

HRID 1766174Notes

Reaction equation

HRID 1766174 reaction equation
[S:1](=[O:5])(=[O:4])([OH:3])[OH:2].CO.[CH3:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][CH:26]3[S:32][C:30](=[O:31])[NH:29][C:27]3=[O:28])=[CH:23][CH:24]=2)=[N:14][CH:15]=1.CCOCC>CCCCCCC>[CH3:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][CH:26]3[S:32][C:30](=[O:31])[NH:29][C:27]3=[O:28])=[CH:23][CH:24]=2)=[N:14][CH:15]=1.[S:1]([O-:5])([O-:4])(=[O:3])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 4829Pioglitazone

Product 1

HCID 11476502HCID 11476502, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

24 g of sulfuric acid was added slowly, at room temperature, to 250 ml of methanol followed by addition of 80 g of pioglitazone base with stirring. The mixture turned into a clear solution. 250 ml of ether was slowly added followed by 500 ml of heptane. A solid precipitated, and the suspension was stirred for 3 hours. The solid (98.4 g, yield was 96.5%) was collected by filtering and washed once with ether. The solid had a mp: 1113.5˜116.5° C. (recrystallized from methanol).

Workup

  1. customA solid precipitated
  2. stirringthe suspension was stirred for 3 hours

Sources & evidence

ORD record
ord-3a66b8193e5f4bfc91429a29a15ab257
Source dataset
uspto-grants-2007_06
Patent number
US07230016B2

Reaction notes

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