Pyridine → HCID 9869915, compound

HRID 1589679Notes

Reaction equation

HRID 1589679 reaction equation
[OH:1][C:2]1[C:3]([CH3:31])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][CH2:5]2.N1C=CC=CC=1.[C:38](OC(=O)C)(=[O:40])[CH3:39]>C1C=CC=CC=1>[C:38]([O:1][C:2]1[C:3]([CH3:31])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][CH2:5]2)(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5591TroglitazoneHCID 7918Acetic Anhydride

Product 1

HCID 9869915HCID 9869915, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.725 g of 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione was dissolved in 4 ml of benzene; 400 mg of dry pyridine were added; 0.2 g of acetic anhydride was added dropwise under a nitrogen stream at 5°-10° C.; and the mixture was reacted for 2 days at room temperature. The resulting white crystals were separated by filtration, washed with benzene and vacuum-dried for 30 minutes at 90° C., giving 0.74 g of the benzene mono adduct of 5-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione. This substance was liquefied at 98°-100° C., solidified and again liquefied at 176°-178° C.

Workup

  1. customand the mixture was reacted for 2 days at room temperature
  2. customThe resulting white crystals were separated by filtration
  3. washwashed with benzene
  4. customvacuum-dried for 30 minutes at 90° C.

Sources & evidence

ORD record
ord-250bb826362743cc80703bc38da66a23
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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