Sodium Carbonate → HCID 19867703, compound

HRID 1198936Notes

Reaction equation

HRID 1198936 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[CH3:12][C:13]1[NH:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH3:8][C:6]1[CH:7]=[C:2]([N:14]2[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=[C:13]2[CH3:12])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 119842-MethylbenzimidazoleHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 19867703HCID 19867703, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-fluoro-2-nitrotoluene (10.3 g), 2-methylbenzimidazole (8.7 g) and sodium carbonate (7.5 g) was heated with stirring in dimethylformamide (40 cm3) at 130° for 16 hours under nitrogen. The cooled mixture was evaporated in vacuo, water (50 cm3) added and the mixture extracted with methanol:chloroform, 1:10 by volume. The combined and dried (MgSO4) organic extracts were evaporated in vacuo to give a residue which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with ethyl acetate. Combination and evaporation of appropriate fractions afforded a solid which was recrystallised from hexane/acetone to give the title compound, m.p. 144°-6°, (10.65 g).

Workup

  1. temperaturewas heated
  2. customThe cooled mixture was evaporated in vacuo, water (50 cm3)
  3. additionadded
  4. extractionthe mixture extracted with methanol
  5. dry with materialdried (MgSO4) organic extracts
  6. customwere evaporated in vacuo
  7. customto give a residue which
  8. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  9. washeluting with ethyl acetate
  10. customCombination and evaporation of appropriate fractions
  11. customafforded a solid which
  12. customwas recrystallised from hexane/acetone

Sources & evidence

ORD record
ord-6e3793958601482d98f051e5d3d17b09
Source dataset
uspto-grants-1990_02
Patent number
US04898872

Reaction notes

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