Formic Acid → 5-Bromo-4-methyl-1H-benzo[d]imidazole

HRID 475241Notes

Reaction equation

HRID 475241 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.Cl.[NH4+].[OH-].[CH:14](O)=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][CH:14]=[N:9][C:4]=2[C:3]=1[CH3:10]

Participants

5

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 592142734-Bromo-3-methylbenzene-1,2-diamine

Product 1

HCID 592144445-Bromo-4-methyl-1H-benzo[d]imidazoleYield 98%

Conditions

Temperature
60 °C

Procedure

A mixture of 156 (28 g, 140 mmol), formic acid (240 mL) and 37% concentrated HCl (400 mL) was heated to 60° C. for 12 h, cooled in an ice-water bath, and the pH slowly adjusted to 8-9 with 28% concentrated NH4OH. The solid was collected by filtration, washed with water and dried in air to afford 25 g (98%) of 5-bromo-4-methyl-1H-benzo[d]imidazole (158) as a yellow solid: MS (ESI) m/z=213 [M+1]+.

Workup

  1. temperaturecooled in an ice-water bath
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customdried in air

Sources & evidence

ORD record
ord-703b875ebec1469ab70aea33134791c1
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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