Pyridine → Phenyl carbamate

HRID 1909077Notes

Reaction equation

HRID 1909077 reaction equation
[C:1]1([O:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:11]1C=CC=CC=1>CC#N.CCOC(C)=O>[C:8](=[O:9])([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[NH2:11]

Participants

5

Reactant 2

HCID 1049PyridineHCID 15891Phenyl chloroformate

Product 1

HCID 69322Phenyl carbamate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Intermediates 10 to 18 were prepared by treatment of the appropriate aminoheterocycle intermediate with 1 equivalent of phenylchloroformate in dry CH3CN and 1 equivalent of pyridine. The reagents were stirred at rt for 4 h, diluted with EtOAc, washed with NaHCO3, and dried over MgSO4. The material was purified by FCC to provide pure phenyl carbamate intermediates.

Workup

  1. washwashed with NaHCO3
  2. dry with materialdried over MgSO4
  3. customThe material was purified by FCC

Sources & evidence

ORD record
ord-40cbfc5d25224577847b8c6d060c70de
Source dataset
uspto-grants-2013_12
Patent number
US08598356B2

Reaction notes

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