Formic Acid → 2-(7-bromo-1H-benzimidazol-1-yl)ethanol

HRID 1991185Notes

Reaction equation

HRID 1991185 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[NH:9][CH2:10][CH2:11][OH:12].Cl.[CH:14](O)=O>>[Br:8][C:4]1[C:3]2[N:9]([CH2:10][CH2:11][OH:12])[CH:14]=[N:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 112069902-[(2-Amino-6-bromophenyl)amino]ethanol

Product 1

HCID 113454912-(7-bromo-1H-benzimidazol-1-yl)ethanol

Procedure

2-[(2-Amino-6-bromophenyl)amino]ethanol (0.14 g, 0.54 mmol) was dissolved in formic acid (3 mL) and irradiated in microwave oven at 135° C. for 2 h. The mixture was cooled and treated with 37% hydrochloric acid (1 mL) at 50° C. for 0.5 h. The volatiles were removed under reduced pressure. The residue was partitioned between ethyl acetate and to saturated aqueous sodium bicarbonate. The organic phase was washed with water and brine, dried over sodium sulfate and concentrated to yield 2-(7-bromo-1H-benzimidazol-1-yl)ethanol, 0.14 g (90%). MS (ESI) m/z: 241.09 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 3.76 (q, J=5.5 Hz, 2H) 4.55 (t, J=5.4 Hz, 2H) 4.97 (t, J=5.4 Hz, 1H) 7.12 (m, 1H) 7.43 (m, 1H) 7.66 (dd, J=8.0, 1.0 Hz, 1H) 8.19 (s, 1H).

Workup

  1. customirradiated in microwave oven at 135° C. for 2 h
  2. temperatureThe mixture was cooled
  3. customThe volatiles were removed under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and to saturated aqueous sodium bicarbonate
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9f554fb39a4144d48144b96c4f761d5e
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

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