Pyridine → Benzyl (2,4-difluorophenyl)carbamate

HRID 1690019Notes

Reaction equation

HRID 1690019 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].N1C=CC=CC=1.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>ClCCl>[CH2:20]([O:19][C:17](=[O:18])[NH:4][C:3]1[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:2]=1[F:1])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 97092,4-DifluoroanilineHCID 10387Benzyl chloroformate

Product 1

HCID 11954520Benzyl (2,4-difluorophenyl)carbamateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2,4-difluoroaniline (19, 7.0 mL, 70.0 mmol) in 100 mL of dichloromethane, pyridine (11 mL, 0.14 mol) and benzyl chloroformate (20, 11.9 mL, 83.4 mmol) were added. The reaction mixture was stirred at ambient temperature for 1.5 hours. The reaction mixture was concentrated under vacuum and the residue was partitioned between ethyl acetate and postassium bisulfate solution. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under vacuum. The resulting material was crystallized from hexanes to provide the desired compound (21, 15.6 g, 85%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was partitioned between ethyl acetate and postassium bisulfate solution
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting material was crystallized from hexanes

Sources & evidence

ORD record
ord-abd31c38828046b7860f5f5de55e741f
Source dataset
uspto-grants-2012_04
Patent number
US08153641B2

Reaction notes

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