Water → HCID 70546223, compound
Reaction equation
[OH:1][C:2]1[C:3]([CH2:8][C:9]2[NH:10][CH:11]=[CH:12][N:13]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[C:16]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1)#[N:17].O>CN(C)C=O>[C:16]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22][O:1][C:2]2[C:3]([CH2:8][C:9]3[NH:13][CH:12]=[CH:11][N:10]=3)=[N:4][CH:5]=[CH:6][CH:7]=2)=[CH:20][CH:19]=1)#[N:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 3-hydroxy-2-(1-imidazolylmethyl)-pyridine (6.0 g) in dry N,N-dimethylformamide (100 ml) was cooled to 5° C. and stirred under nitrogen. Sodium hydride (1.8 g as a dispersion in mineral oil) was added and the mixture was stirred for 1 hour at room temperature and then cooled to 0° C. A solution of 4-cyano-benzylbromide (6.8 g) in dry N,N-dimethylformamide (25 ml) was added and the mixture stirred at room temperature for a further 3 hours and allowed to stand overnight. Water (250 ml) was added and the aqueous solution extracted with ethyl acetate (4×100 ml). The organic extracts were combined, washed with water, dried over MgSO4 and evaporated to yield a solid. Recrystallization from ethyl acetate gave 3-(4-cyanobenzyloxy)-2-(1-imidazolylmethyl)pyridine (12.0 g), m.p. 159° C.
Workup
- stirringthe mixture was stirred for 1 hour at room temperature
- stirringthe mixture stirred at room temperature for a further 3 hours
- extractionthe aqueous solution extracted with ethyl acetate (4×100 ml)
- washwashed with water
- dry with materialdried over MgSO4
- customevaporated
- customto yield a solid
- customRecrystallization from ethyl acetate
Sources & evidence
- ORD record
- ord-eb42d0a8ecfa4771861a1b15554e703d
- Source dataset
- uspto-grants-1982_07
- Patent number
- US04339583
Reaction notes
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