Sodium Hydroxide → HCID 15166268, compound
Reaction equation
[OH-].[Na+].[Cl:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([CH2:16]Cl)[C:11]=1[CH3:18].ClCC1C(C)=C(OCCOCCO)C=CN=1.OCC1C(C)=C(OCCOCCO)C=CN=1.[SH:51][C:52]1[NH:56][C:55]2[CH:57]=[CH:58][CH:59]=[CH:60][C:54]=2[N:53]=1>>[Cl:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([CH2:16][S:51][C:52]2[NH:56][C:55]3[CH:57]=[CH:58][CH:59]=[CH:60][C:54]=3[N:53]=2)[C:11]=1[CH3:18]Participants
Conditions
- Temperature
- 60 °C
Procedure
0.54 g of sodium hydroxide was added to an ethanolic solution of 3.1 g of a crude mixture comprising 4-[2-(2-chloroethoxy)ethoxy]-2-chloromethyl-3-methylpyridine and 2-chloromethyl-4-[2-(2-hydroxyethoxy)ethoxy]-3-methylpyridine which has been prepared by the chlorination of 2-hydroxymethyl-4-[2-(2-hydroxyethoxy)ethoxy]-3-methylpyridine and 2.0 g of 2-mercapto-1H-benzimidazole to obtain a mixture. This mixture was stirred at 60° C. for 1.5 hour, cooled and distilled under a reduced pressure to remove the ethanol. The obtained residue was chromatographed over a silica gel column and eluted with ethyl acetate/n-hexane and then with methanol/ethyl acetate to obtain 1.0 g of 2-[{4-(2-(2-chloroethoxy)ethoxy)-3-methylpyridine-2-yl}methylthio]-1H-benzimidazole
Workup
- customto obtain a mixture
- temperaturecooled
- distillationdistilled under a reduced pressure
- customto remove the ethanol
- customThe obtained residue was chromatographed over a silica gel column
- washeluted with ethyl acetate/n-hexane
Sources & evidence
- ORD record
- ord-d624d032884644c69584e5793675754d
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05840910
Reaction notes
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