1-(p-Tolyl)cyclopropanecarboxylic acid → HCID 18400145, compound

HRID 1019078

Reaction equation

HRID 1019078 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.F[B-](F)(F)F.[O:19]=[N+:20]=[O:21]>S1(CCCC1)(=O)=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([OH:13])=[O:12])[CH2:9][CH2:10]2)=[CH:6][C:7]=1[N+:20]([O-:21])=[O:19]

Participants

4

Reactant 2

HCID 986391-(p-Tolyl)cyclopropanecarboxylic acidHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 18400145HCID 18400145, compound

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

Commercially available 1-(4-methylphenyl)-1-cyclopropane carboxylic acid is treated with nitronium tetrafluoroborate in sulfolane to afford 1-(4-methyl-3-nitrophenyl)-1-cyclopropane carboxylic acid. This is converted to 1-(4-methyl-3-nitrophenyl)-1-bromocyclopropane by treatment with mercuric oxide and bromine in methylene chloride. Reduction with zinc dust in the presence of calcium chloride in aqueous ethanol affords 5-cyciopropyl-2-methylaniline. Conversion to 4-cyclopropyl-5-(2-imidazolinylamino)-7-methylbenzimidazole is completed in the same manner as 4-ethyl-5-(2-imidazolinylamino)-7-methylbenzimidazole (see Example 2).

Sources & evidence

ORD record
ord-4f369910b121440998f40a296777283f
Source dataset
uspto-grants-2002_11
Patent number
US06486190B1

Linked notes

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