Ethyl orthoformate → HCID 178486900, compound

HRID 1848011Notes

Reaction equation

HRID 1848011 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]([NH2:10])=[CH:6][C:7]=1[O:8][CH3:9].[CH:12](OCC)(OCC)OCC>C(O)=O>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]2[NH:10][CH:12]=[N:11][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 133035714-Bromo-5-methoxybenzene-1,2-diamine

Product 1

HCID 178486900HCID 178486900, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a stirred mixture of 4-bromo-5-methoxybenzene-1,2-diamine (3.8 g, 18 mmol) from Step 1 of this Example and triethyl orthoformate (50 mL) was added formic acid (1 mL). The mixture was heated at reflux for 3 h, then concentrated under reduced pressure. The residue was partitioned between EtOAc (200 mL) and a 1 N aq Na2CO3 (100 mL). The EtOAc layer was separated, washed with brine (100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 5-bromo-6-methoxy-1H-benzo[d]imidazole (4.0 g) as a brown oil. The material was used in the next step without further purification. LCMS (ESI) m/z 228 and 230 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between EtOAc (200 mL)
  5. customThe EtOAc layer was separated
  6. washwashed with brine (100 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f69d5c05eb224f6f98cf0c651b1fcde6
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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