Water → HCID 54023400, compound

HRID 2211292Notes

Reaction equation

HRID 2211292 reaction equation
[CH2:1]([S:3][C:4]1[NH:5][C:6]2[C:7](=[C:9]([C:13]([O:15][CH3:16])=[O:14])[S:10][C:11]=2[CH3:12])[N:8]=1)[CH3:2].[H-].[Na+].[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:32]=[CH:31][C:30]([CH2:33]Br)=[CH:29][CH:28]=1)#[N:20].O>CN(C=O)C>[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:28]=[CH:29][C:30]([CH2:33][N:8]2[C:7]3=[C:9]([C:13]([O:15][CH3:16])=[O:14])[S:10][C:11]([CH3:12])=[C:6]3[N:5]=[C:4]2[S:3][CH2:1][CH3:2])=[CH:31][CH:32]=1)#[N:20]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 178418569HCID 178418569, compound

Product 1

HCID 54023400HCID 54023400, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of methyl 2-ethylthio-4-methylthieno[3,4-d]imidazole-6-carboxylate (5.7 g) in DMF (30 ml) was added sodium hydride (60% oil, 0.98 g) under ice-cooling. After stirring the reaction mixture for 20 minutes, to the mixture was added dropwise a solution of (2'-cyanobiphenyl-4-yl)methyl bromide (7.25 g) in DMF (20 ml), followed by stirring for one hour at room temperature. To the reaction mixture was added water, which was extracted with ethyl acetate. The extract was washed with water and dried, then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography to give crystals. Recrystallization from ethyl acetate - hexane afforded pale yellow prisms (7.6 g, 77%), m.p. 149°-151° C.

Workup

  1. temperaturecooling
  2. stirringby stirring for one hour at room temperature
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. customto give crystals
  9. customRecrystallization from ethyl acetate - hexane afforded pale yellow prisms (7.6 g, 77%), m.p. 149°-151° C.

Sources & evidence

ORD record
ord-10fcaf7ab5ed444784ac0f8a15189fbc
Source dataset
uspto-grants-1995_10
Patent number
US05463073

Reaction notes

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