Formic Acid → HCID 178419331, compound

HRID 475200Notes

Reaction equation

HRID 475200 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[CH:10](O)=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][CH:10]=[N:9][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 3235934-Bromobenzene-1,2-diamine

Product 1

HCID 178419331HCID 178419331, compoundYield 100%

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromobenzene-1,2-diamine (4.0 g, 21.5 mmol) and formic acid (95%, 100 mL) was stirred at 100° C. overnight. The reaction mixture was cooled to RT and concentrated in vacuo to afford a dark oil. The crude oil was partitioned between EtOAc (500 mL) and NH3/H2O (50 mL). The EtOAc layer was separated and concentrated in vacuo to afford 4.5 g (100%) of 5-bromo-1H-benzo[d]imidazole (78) as brown solid: MS (ESI) m/z=197.0 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. concentrationconcentrated in vacuo
  3. customto afford a dark oil
  4. customThe crude oil was partitioned between EtOAc (500 mL) and NH3/H2O (50 mL)
  5. customThe EtOAc layer was separated
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2cdb7cd6e94c4ed4b6a3107380ddf1cd
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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