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

HRID 1622494Notes

Reaction equation

HRID 1622494 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].[CH:13]1([C:16](O)=O)[CH2:15][CH2:14]1.Cl.[OH-].[Na+]>>[Br:1][C:2]1[C:3]2[N:12]=[C:16]([CH:13]3[CH2:15][CH2:14]3)[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 14798Sodium HydroxideHCID 15655Cyclopropanecarboxylic acidHCID 203480123-Bromo-5-nitrobenzene-1,2-diamine

Product 1

HCID 866878504-bromo-2-cyclopropyl-6-nitro-1H-benzo[d]imidazoleYield 88.4%

Conditions

Temperature
105 °C

Procedure

In a 250 mL round-bottom flask a mixture of 3-bromo-5-nitrobenzene-1,2-diamine (4 g, 17.24 mmol) and cyclopropanecarboxylic acid (14.06 ml, 155 mmol) in 3M HCl (40 ml, 120 mmol) was heated to 105° C. for 5 days. The mixture was allowed to cool to room temperature and was poured into chilled 5M NaOH (25 ml, 125 mmol) solution. The resulting mixture was allowed to stand in an icebath 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. The resulting dark solid 4-bromo-2-cyclopropyl-6-nitro-1H-benzo[d]imidazole (4.3 g, 15.24 mmol, 88% yield) will be used as is in the next step. MS (ES+) m/e: 280.9, 281.8 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-3d4a1dac213a47788c6d8cffe59c38e5
Source dataset
uspto-grants-2014_07
Patent number
US08778937B2

Reaction notes

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