Hydrochloric Acid → HCID 88232456, compound

HRID 324275Notes

Reaction equation

HRID 324275 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.F[C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=[O:15].C([O-])([O-])=O.[K+].[K+].[ClH:25]>CS(C)=O.CCOC(C)=O.CO.CCOC(C)=O.CCCCCC>[ClH:25].[CH:14]([C:13]1[CH:12]=[C:11]([N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[CH:2]2)[CH:18]=[CH:17][CH:16]=1)=[O:15]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 680093-Fluorobenzaldehyde

Product 1

HCID 88232456HCID 88232456, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 21226206Ethyl acetate hexaneSolvent2×HCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of benzimidazole (VIII: R=H) (1.00 g, 8.47 mmol) and 3-fluorobenzaldehyde (IX: R1′=3—CHO; halogen=F) (1.08 mL, 10.2 mmol) in DMSO (30 mL) was heated with anhydrous K2CO3 (2.34 g, 16.9 mmol) for 24 hours at 100° C. to give, after column chromatography on silica gel eluting with EtOAc/hexane (1:1) to EtOAc/hexane (3:1), Example 4 as the HCl salt, mp (EtOAc/MeOH) 196-201° C.

Workup

  1. customto give

Sources & evidence

ORD record
ord-3015f39b5d8f4a1ca2d9dd693e88a309
Source dataset
uspto-grants-2001_04
Patent number
US06218388B1

Reaction notes

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