Hydrochloric Acid → 4-bromo-2-isopropyl-6-nitro-1H-benzo[d]imidazole

HRID 1622489Notes

Reaction equation

HRID 1622489 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([NH2:11])[C:3]=1[NH2:12].[C:13](O)(=O)[CH:14]([CH3:16])[CH3:15].Cl.[OH-].[Na+]>>[Br:1][C:2]1[C:3]2[N:12]=[C:13]([CH:14]([CH3:16])[CH3:15])[NH:11][C:4]=2[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6590Isobutyric AcidHCID 14798Sodium HydroxideHCID 203480123-Bromo-5-nitrobenzene-1,2-diamine

Product 1

HCID 866878464-bromo-2-isopropyl-6-nitro-1H-benzo[d]imidazoleYield 85.7%

Conditions

Temperature
105 °C

Procedure

A mixture of 3-bromo-5-nitrobenzene-1,2-diamine (4 g, 17.24 mmol) and isobutyric acid (7.99 ml, 86 mmol) in 3M HCl (100 ml, 300 mmol) was heated to 105° C. for 5 days. The mixture was allowed to cool to room temperature and was poured into chilled 5M Sodium Hydroxide (60.0 ml, 300 mmol) solution. The resulting mixture was allowed to stand in an ice bath and the brown solid that precipitated was collected by filtration. The solid was washed several times with H2O and then dried in a vacuum oven at 50° C. leaving desired product as a dark solid (4.2 g, 71% yield). MS (ES+) m/e: 283.0, 284.0 [M+H]+

Workup

  1. temperatureto cool to room temperature
  2. additionwas poured
  3. customto stand in an ice bath
  4. filtrationthe brown solid that precipitated was collected by filtration
  5. washThe solid was washed several times with H2O
  6. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-86ef37f8240844b58392e7fa2ecd8a8b
Source dataset
uspto-grants-2014_07
Patent number
US08778937B2

Reaction notes

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