Phosphorodichloridic acid, phenyl ester → HCID 10423520, compound

HRID 890593Notes

Reaction equation

HRID 890593 reaction equation
P(Cl)(Cl)(OC1C=CC=CC=1)=O.[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[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>[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([N:30]=[N+:31]=[N-:32])=[O:19])=[CH:16][C:15]=1[N:23]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]1

Participants

6

Reactant 3

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

Product 1

HCID 10423520HCID 10423520, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

At ambient temperature, add a solution of 5.3 g (0.025 mol) of phenyl dichlorophosphate in 100 ml of dichloromethane to a solution of 5 g (0.02 mol) of 4-methoxy-3-(4-methyl piperazin-1-yl)benzoic acid [J. Med. Chem., 37 (15), 2255 (1994)] and 3.25 g (0.05 mol) of sodium azide in 4.05 ml of pyridine. After stirring for 12 hours, wash the organic phase with 100 ml of water, separate off the organic phase, dry it over magnesium sulphate and evaporate off the solvent in vacuo at 30° C.

Workup

  1. washwash the organic phase with 100 ml of water
  2. customseparate off the organic phase
  3. dry with materialdry it over magnesium sulphate
  4. customevaporate off the solvent in vacuo at 30° C.

Sources & evidence

ORD record
ord-855bf25ff6784a8180c67bc668b74a04
Source dataset
uspto-grants-2006_02
Patent number
US06998403B2

Reaction notes

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