Sodium hydride → HCID 18537617, compound

HRID 412386Notes

Reaction equation

HRID 412386 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:17]=[CH:16][C:7]([CH2:8][CH:9]2[S:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1.Cl[CH2:19][C:20]1[N:40]([CH3:41])[C:23]2=[N:24][C:25]([S:28][C:29]3[CH:34]=[C:33]([CH3:35])[C:32]([N+:36]([O-:38])=[O:37])=[C:31]([CH3:39])[CH:30]=3)=[CH:26][CH:27]=[C:22]2[N:21]=1>CN(C)C=O>[CH3:39][C:31]1[CH:30]=[C:29]([S:28][C:25]2[N:24]=[C:23]3[N:40]([CH3:41])[C:20]([CH2:19][O:3][C:4]4[CH:17]=[CH:16][C:7]([CH2:8][CH:9]5[S:13][C:12](=[O:14])[NH:11][C:10]5=[O:15])=[CH:6][CH:5]=4)=[N:21][C:22]3=[CH:27][CH:26]=2)[CH:34]=[C:33]([CH3:35])[C:32]=1[N+:36]([O-:38])=[O:37]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 101983975-(4-Hydroxybenzyl)thiazolidine-2,4-dioneHCID 18537632HCID 18537632, compound

Product 1

HCID 18537617HCID 18537617, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (0.12 g, 55% w/w) in N,N-dimethylformamide (6 ml) was added 5-(4-hydroxybenzyl)thiazolidine-2,4-dione (0.31 g). The mixture was stirred at room temperature for 20 minutes. To the reaction mixture was added dropwise a solution of 2-chloromethyl-5-(3,5-dimethyl-4-nitrophenylthio)-3-methyl-3H-imidazo[4,5-b]pyridine (0.51 g) in anyhdrous N,N-dimethylformamide (14 ml). The mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated and neutralized with 3N hydrochloric acid and sodium bicarbonate and then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on a silica gel column using ethyl acetate as the eluant to afford the desired compound (0.39 g, Rf=0.60: thin layer chromatography on a silica gel plate using ethyl acetate as the eluant).

Workup

  1. stirringThe mixture was stirred at room temperature for 15 hours
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-a2fc95bb99af4271824081d21aca7932
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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