2-Methoxyethanol → HCID 68960518, compound

HRID 2191780Notes

Reaction equation

HRID 2191780 reaction equation
[C:1](O)(=O)C.C(N)=N.COCCO.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21]1[CH:33]=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[C:23]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[CH:22]=1.C(OCC)(=O)C>O>[N:20]1([C:21]2[CH:33]=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[C:23]([NH:34][C:35]3[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=3)[CH:22]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[CH:1]1

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 8857Ethyl AcetateHCID 160693Formamidine acetateHCID 68962942HCID 68962942, compound

Product 1

HCID 68960518HCID 68960518, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Formamidine acetate 0.10 g was added to ethylene glycol monomethyl ether 3.0 mL solution of tert-butyl 4-((2-aminophenyl)amino)-2-(4-fluoroanilino)benzoate 0.15 g at room temperature, and it was stirred at 80° C. for 6 hours. After the reaction mixture was cooled to room temperature, and ethyl acetate and water were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution, the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=2:1] to give tert-butyl 4-(1H-benzimidazol-1-yl)-2-(4-fluoroanilino)benzoate 0.16 g of a pale red solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washafter sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5ce9d33e20894f5796bdf6c4bd69a20b
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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