Water → 2-fluoro-5-methoxy-4-(1-methyl-1H-benzimidazol-2-ylmethoxy)-benzaldehyde

HRID 253474

Reaction equation

HRID 253474 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].Cl[CH2:16][C:17]1[N:21]([CH3:22])[C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[N:18]=1.O>CN(C)C(=O)C>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:16][C:17]2[N:21]([CH3:22])[C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[N:18]=2)[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2480442-(Chloromethyl)-1-methylbenzimidazoleHCID 5981552-Fluoro-4-hydroxy-5-methoxybenzaldehyde

Product 1

HCID 598038732-fluoro-5-methoxy-4-(1-methyl-1H-benzimidazol-2-ylmethoxy)-benzaldehydeYield 267.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-fluoro-4-hydroxy-5-methoxy-benzaldehyde (39, 3.0 g, 5 mmol) in N,N-dimethylacetamide (120 mL) was added sodium hydride (60% dispersion in mineral oil, 0.8 g, 19 mmol) portion wise. After the addition was complete, the reaction was stirred for 30 minutes after which 2-chloromethyl-1-methyl-1H-benzoimidazole (212, 2.9 g, 16 mmol) was added and then heated at 80° C. overnight. The reaction mixture was then poured into water (1 L) with stirring and the precipitated solid was filtered, washed with water and dried to give the desired compound (213, 4.2 g, 84% yield).

Workup

  1. additionAfter the addition
  2. additionwas added
  3. filtrationthe precipitated solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5745c0bd33554da4aea5d3f33ddc96d3
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Linked notes

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