Dimethylformamide → HCID 68459564, compound

HRID 1042659Notes

Reaction equation

HRID 1042659 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.[NH:16]1[CH:20]=C[C:18]([CH2:21][OH:22])=[CH:17]1.C([O-])([O-])=O.[Na+].[Na+].C[N:30](C=O)C>>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[N:16]1[CH:17]=[C:18]([CH2:21][OH:22])[N:30]=[CH:20]1)([O-:14])=[O:13]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 68462588HCID 68462588, compound

Product 1

HCID 68459564HCID 68459564, compound

Conditions

Temperature
70 °C

Procedure

To a solution of 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (1.04 mL, 7.43 mmol) and (1H-pyrrol-3-yl)methanol hydrochloride salt (1.0 g, 7.43 mmol) in DMF (10 mL) was added Na2CO3 (2.36 g, 22.3 mmol). The resulting mixture was heated at 70° C. overnight. The mixture was cooled to room temperature and concentrated under reduced pressure. The mixture was reconstituted in EtOAc (50 mL) and washed with 9% aq. Na2CO3 (10 mL), brine (10 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford (1-(2-nitro-4-(trifluoromethyl)phenyl)-1H-imidazol-4-yl)methanol.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. washwashed with 9% aq. Na2CO3 (10 mL), brine (10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e644dc441d01411488a1bbc66e8bb0a2
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

Loading…