Hydrochloric Acid → HCID 178419331, compound

HRID 1399936Notes

Reaction equation

HRID 1399936 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[CH:10](OC)(OC)OC.Cl.C([O-])(O)=O.[Na+]>CN(C=O)C.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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9005Trimethyl orthoformateHCID 3235934-Bromobenzene-1,2-diamineHCID 516892Sodium Bicarbonate

Product 1

HCID 178419331HCID 178419331, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromobenzene-1,2-diamine (3 g, 16 mmol) in DMF (22 mL) were added trimethyl orthoformate (44 mL) and conc. HCl (1.5 mL) and the mixture was stirred at room temperature for 1 h. The mixture was diluted with water (200 mL) and adjusted to pH7 with saturated aqueous NaHCO3, extract with ethyl acetate (200 mL). The organic layer was dried over Na2SO4, concentrated to give 5-bromo-1H-benzo[d]imidazole (3.25 g, 100%) as an off-white solid. LCMS: 197 [M+1]+. 1H NMR (400 MHz, DMSO-d6) δ 7.33 (t, J=8.8 Hz, 1H), 7.55 (dd, J1=7.6 Hz, J=40 Hz, 1H), 7.79 (d, J=47.2 Hz, 1H), 8.26 (s, 1H), 12.61 (d, J=25.6 Hz, 1H).

Workup

  1. extractionextract with ethyl acetate (200 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a98c49ad92134dbab9f541c05f76a050
Source dataset
uspto-grants-2014_12
Patent number
US08906909B2

Reaction notes

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