Pyridine → HCID 57656651, compound

HRID 2371155Notes

Reaction equation

HRID 2371155 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:12][C:23](=[O:24])[O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 928923-Benzyloxyaniline

Product 1

HCID 57656651HCID 57656651, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-benzyloxyaniline (0.999 g, 5.01 mmol) in DCM (10 mL) was added pyridine (1.22 ml, 15.03 mmol) and phenyl chloroformate (0.68 ml, 5.51 mmol) dropwise (Exotherm!). The reaction was then allowed to stir at room temperature for 2 hours. The reaction mixture was then partitioned between DCM and 1M HCl, extracted twice, combined organics passed through phase separating cartridge and filtrate evaporated to dryness to give an orange solid. This was then triturated in 10% ethyl acetate/hexanes, filtered and dried to give the product, phenyl [3-(benzyloxy)phenyl]carbamate, as beige solid (1.209 g, 3.78 mmol, 75% yield).

Workup

  1. customThe reaction mixture was then partitioned between DCM and 1M HCl
  2. extractionextracted twice
  3. customseparating cartridge and filtrate
  4. customevaporated to dryness
  5. customto give an orange solid
  6. customThis was then triturated in 10% ethyl acetate/hexanes
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-9bd63c0b6b9a447086810ad188b38dc1
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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