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

HRID 1427344Notes

Reaction equation

HRID 1427344 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-5c29c17b976346a0ac07e50a7ba43e13
Source dataset
uspto-grants-2015_01
Patent number
US08933224B2

Reaction notes

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