Water → HCID 18924848, compound

HRID 1288824Notes

Reaction equation

HRID 1288824 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.Cl[CH2:9][C:10]1[N:15]=[C:14]2[S:16][C:17]([CH3:20])=[C:18]([CH3:19])[C:13]2=[C:12]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[C:11]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29].O>CN(C)C=O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:12]2[C:11]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:10]([CH2:9][N:3]3[CH:7]=[N:6][CH:5]=[N:4]3)[N:15]=[C:14]3[S:16][C:17]([CH3:20])=[C:18]([CH3:19])[C:13]=23)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 18924845HCID 18924845, compound

Product 1

HCID 18924848HCID 18924848, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 0.158 g) was added to a solution of 1H-1,2,4-triazole (0.252 g) in N,N-dimethylformamide (DMF) (15 ml). The mixture was stirred for 15 minutes at room temperature, to which was added ethyl 6-chloromethyl-4-(4-chlorophenyl)-2,3-dimethylthieno[2,3-b]pyridine-5-carboxylate (1.2 g). The mixture was stirred for 35 minutes at 80° C. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off. The residue was subjected to column chromatography on silica gel. From the fraction eluted with dichloromethane-ethyl acetate (20:1, v/v), was obtained ethyl 4-(4-chlorophenyl)-2,3-dimethyl-6-(1,2,4-triazol-1-ylmethyl)thieno[2,3-b]pyridine-5-carboxylate (0.655 g, 50%). Recrystallization from ethanol gave colorless prisms, m.p.144°-145° C.

Workup

  1. stirringThe mixture was stirred for 35 minutes at 80° C
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off
  6. washFrom the fraction eluted with dichloromethane-ethyl acetate (20:1

Sources & evidence

ORD record
ord-d9812c6a17614d12a5d210b9d1e5ed8e
Source dataset
uspto-grants-1998_05
Patent number
US05747486

Reaction notes

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