Sodium Hydroxide → 2-[[(4-Methoxy)pyridin-2-yl]methylthio]-6-fluoro-5-(imidazol-1-yl)-1H-benzimidazole

HRID 1004591Notes

Reaction equation

HRID 1004591 reaction equation
[F:1][C:2]1[C:3]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:4][C:5]2[N:9]=[C:8]([SH:10])[NH:7][C:6]=2[CH:11]=1.Cl.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([CH2:26]Cl)[CH:21]=1.[OH-].[Na+].[K+].[Br-]>C(O)C>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([CH2:26][S:10][C:8]2[NH:7][C:6]3[CH:11]=[C:2]([F:1])[C:3]([N:12]4[CH:16]=[CH:15][N:14]=[CH:13]4)=[CH:4][C:5]=3[N:9]=2)[CH:21]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 253877Potassium BromideHCID 139233682-(Chloromethyl)-4-methoxypyridine hydrochlorideHCID 178505406HCID 178505406, compound

Product 1

HCID 539610442-[[(4-Methoxy)pyridin-2-yl]methylthio]-6-fluoro-5-(imidazol-1-yl)-1H-benzimidazoleYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound (1.9 g, 60%) was prepared by the general procedure using, 6-fluoro-5-(imidazol-1-yl)-2-mercapto-1H-benzimidazole (2.1 g, 9.0 mmol), (obtained in preparation 1) 4-methoxy-2-chloromethylpyridine hydrochloride (1.74 g, 9.0 mmol), sodium hydroxide (0.72 g, 18.0 mmol) and ethanol (25 mL). mp 86-87° C.; IR (KBr) 3443, 1600 cm-1 ; 1H NMR (CDCl3) δ 3.90 (s, 3H, OCH3), 4.38 (s, 2H, SCH2), 6.92 (d, J=5.7 Hz, 1H), 6.96 (s, 1H), 7.30 (m, 2H), 7.42 (d, J=10.2 Hz, 1H), 7.58 (d, J=7.8 Hz, 1H), 7.80 (s, 1H), 8.50 (d, J=6.0 Hz, 1H), 14.00 (brs, 1H, NH); Mass (m/z) 355 (M+.).

Sources & evidence

ORD record
ord-6b66498da5174317a4e17f7759a4cb04
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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