Pyridine → Benzyl (2,4-difluorophenyl)carbamate

HRID 1187285Notes

Reaction equation

HRID 1187285 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-difluoro-phenylamine (30, 7.0 mL, 70.0 mmol) in 100 mL of dichloromethane, pyridine (11 mL, 0.14 mol) and benzyl chloroformate (31, 11.9 mL, 83.4 mmol) are added. The reaction mixture is stirred at ambient temperature for 1.5 hours. The reaction mixture is concentrated under vacuum and the residue is partitioned between ethyl acetate and potassium bisulfate solution. The organic layer is dried with magnesium sulfate, filtered, and the filtrate concentrated under vacuum. The resulting material is crystallized from hexanes to provide the desired compound (32, 15.6 g, 85%).

Workup

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

Sources & evidence

ORD record
ord-7b50e0b8e6ee4460a6de76c0dd33449b
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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