Phosphorodichloridic acid, phenyl ester → HCID 22186073, compound

HRID 1837501Notes

Reaction equation

HRID 1837501 reaction equation
P(Cl)(Cl)([O:3][C:4]1C=CC=CC=1)=O.CO[C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][C:15]=1[N:23]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]1.[N-:30]=[N+:31]=[N-:32].[Na+]>ClCCl.N1C=CC=CC=1>[CH3:4][O:3][C:21]1[CH:22]=[CH:14][C:15]([N:23]2[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]2)=[CH:16][C:17]=1[C:18]([N:30]=[N+:31]=[N-:32])=[O:20]

Participants

6

Reactant 3

HCID 13038Phosphorodichloridic acid, phenyl esterHCID 33557Sodium AzideHCID 10014996HCID 10014996, compound

Product 1

HCID 22186073HCID 22186073, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 25 mmol (5.3 g) of phenyl dichlorophosphate in 100 ml of dichloromethane is added to a solution of 20 mmol (5 g) of 4-methoxy-3-(4-methyl-1-piperazinyl)benzoic acid (described in J. Med. Chem., 1994, 37, p.2255) and 50 mmol (3.25 g) of sodium azide in 4.05 ml of pyridine. After stirring for 12 hours at ambient temperature, the organic phase is washed with 100 ml of water, dried over magnesium sulphate and concentrated to yield the expected product.

Workup

  1. washthe organic phase is washed with 100 ml of water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4931824eb99944ccbfc9a57d66ff3c10
Source dataset
uspto-grants-2004_08
Patent number
US06784183B2

Reaction notes

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