4-Chloro-5-fluoro-1,2-phenylenediamine → 5-chloro-6-fluoro-2-methyl-1H-benzimidazole

HRID 658093

Reaction equation

HRID 658093 reaction equation
[C:1]([O-])([O-])(OCC)[CH3:2].[Cl:8][C:9]1[CH:10]=[C:11]([NH2:17])[C:12]([NH2:16])=[CH:13][C:14]=1[F:15]>C(O)C>[Cl:8][C:9]1[C:14]([F:15])=[CH:13][C:12]2[NH:16][C:1]([CH3:2])=[N:17][C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 7357734-Chloro-5-fluoro-1,2-phenylenediamineHCID 86598186Ethyl ortho-acetate

Product 1

HCID 552815655-chloro-6-fluoro-2-methyl-1H-benzimidazoleYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A 4.96 g portion of ethyl orthoacetate dissolved in 10 ml of ethanol was added to 50 ml of ethanol solution containing 4.68 g of 4-chloro-5-fluorobenzene-1,2-diamine and heated under reflux for 4 hours. After concentration of the reaction liquid, the thus formed residue was purified by a silica gel column chromatography to obtain 2.10 g (39%) of 5-chloro-6-fluoro-2-methyl-1H-benzimidazole from a chloroform-methanol (10:1) eluate. ES+: 185

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. customAfter concentration of the reaction liquid
  4. customthe thus formed residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-3808743c057d473893bf85eb35750524
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Linked notes

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