Ethyl orthoformate → 5-Fluorobenzimidazole

HRID 2191924Notes

Reaction equation

HRID 2191924 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[CH2:10](OC(OCC)OCC)C>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[CH:10][NH:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 1645844-Fluorobenzene-1,2-diamine

Product 1

HCID 2356985-Fluorobenzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

To the solution of 4-fluoro-benzene-1,2-diamine (10 g, 79.4 mmol) and triethylorthoformate (117 mL, 793 mmol) was added few drop of ethanol and the reaction mixture was refluxed at 150° C. overnight. The reaction mixture was concentrated and the residue was directly taken to the next step. [M+H]=137.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-f2ff2e146fad4178aa5667e0c91fe0c0
Source dataset
uspto-grants-2012_12
Patent number
US08329700B2

Reaction notes

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