2,4,6-Trimethylpyridine → 4-Nitrophenyl hydrogen carbonimidate

HRID 2279683Notes

Reaction equation

HRID 2279683 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].CC1C=C(C)[N:18]=C(C)C=1>ClCCl>[C:2](=[O:3])([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)[NH2:18]

Participants

4

Reactant 2

HCID 79532,4,6-TrimethylpyridineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 1699564-Nitrophenyl hydrogen carbonimidate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Para-nitrophenyl chloroformate (483 mg, 2.40 mmol) was dissolved in 10 mL dichloromethane (dry, mol. sieve). A solution of amine 18d (1.00 g, 2.31 mmol) in 5 mL dichloromethane (dry, mol. sieve) and 1.8 mL of sym-collidine were added and mixture was stirred at room temperature for 40 min. Dichloromethane was removed under reduced pressure, residue was acidified with acetic acid and purified by RP-HPLC to yield para-nitrophenyl carbamate 18e.

Workup

  1. customDichloromethane was removed under reduced pressure, residue
  2. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-a22b98833da2482d90eb93646a426d3a
Source dataset
uspto-grants-2015_09
Patent number
US09133276B2

Reaction notes

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