Trifluoroacetic acid → 4-(2-fluorophenyl)-2-methyl-1H-imidazol-1-amine

HRID 931334Notes

Reaction equation

HRID 931334 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH3:21])[N:11]([NH:13]C(=O)OC(C)(C)C)[CH:12]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH3:21])[N:11]([NH2:13])[CH:12]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 117682912tert-butyl[4-(2-fluorophenyl)-2-methyl-1H-imidazol-1-yl]carbamate

Product 1

HCID 1176783184-(2-fluorophenyl)-2-methyl-1H-imidazol-1-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound C2 (17.4 g, 59.7 mmol) in dichloromethane (120 mL) was treated with trifluoroacetic acid (23.0 mL, 299 mmol) and allowed to stir for 18 hours at room temperature. Excess 1 N aqueous sodium hydroxide solution was added, and the mixture was stirred vigorously for 15 minutes. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the product as a brown solid. Yield: 9.95 g, 52.0 mmol, 87%. LCMS m/z 192.3 [M+H]+.

Workup

  1. stirringthe mixture was stirred vigorously for 15 minutes
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e371db94b6054dffbaef7eb17907daea
Source dataset
uspto-grants-2016_03
Patent number
US09296761B2

Reaction notes

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