Trifluoroacetic acid → HCID 178458929, compound

HRID 475675Notes

Reaction equation

HRID 475675 reaction equation
[Br:1][C:2]1[N:6]=[C:5]([O:7][CH2:8][CH2:9][CH3:10])[N:4](COCC[Si](C)(C)C)[C:3]=1[CH:19]=[O:20].C(O)(C(F)(F)F)=O>>[Br:1][C:2]1[N:6]=[C:5]([O:7][CH2:8][CH2:9][CH3:10])[NH:4][C:3]=1[CH:19]=[O:20]

Participants

3

Conditions

Temperature
0 °C

Procedure

5-Bromo-2-propoxy-3-(2-trimethylsilanylethoxymethyl)-3H-imidazole-4-carbaldehyde (43.6 g, 120 mmol) was cooled at 0° C. in ice. TFA (200 mL, 2 mol) was added and the mixture was stirred at 0° C. for 15 minutes, then warmed to room temperature. After 20 minutes, the mixture was concentrated under reduced pressure and redissolved in EtOAc (300 mL). The organic was washed with saturated bicarbonate (200 mL), saturated aqueous NaCl, dried over MgSO4 and concentrated under reduced pressure to produce the title compound (28.6 g) as a yellow solid, which was used without further purification.

Workup

  1. temperaturewarmed to room temperature
  2. waitAfter 20 minutes
  3. concentrationthe mixture was concentrated under reduced pressure
  4. dissolutionredissolved in EtOAc (300 mL)
  5. washThe organic was washed with saturated bicarbonate (200 mL), saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-61d2a330b69d4fa39056d5a052ad0aab
Source dataset
uspto-grants-2014_01
Patent number
US08637562B2

Reaction notes

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