Formic Acid → 4-Bromo-1H-benzimidazole

HRID 1051514Notes

Reaction equation

HRID 1051514 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].[CH:10](O)=O>>[Br:1][C:2]1[C:3]2[N:9]=[CH:10][NH:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 124898393-Bromobenzene-1,2-diamine

Product 1

HCID 112525844-Bromo-1H-benzimidazoleYield 80%

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromobenzene-1,2-diamine (2 g, 10.7 mmol) in HCOOH was stirred at 100° C. for 1 h. The mixture was cooled and concentrated in vacuo and diluted with ethyl acetate and aq. NaHCO3. The mixture was extracted further with ethyl acetate and the combined organic layers dried and concentrated to give the crude product which was purified by column chromatography to obtain the desired product (1.65 g, Yield 80%). LCMS (m/z): 197.0 (M+1).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. additiondiluted with ethyl acetate and aq. NaHCO3
  4. extractionThe mixture was extracted further with ethyl acetate
  5. customthe combined organic layers dried
  6. concentrationconcentrated
  7. customto give the crude product which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ae5adcf2a5774a20b1f34eabc602b719
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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