Tert-Butyl nitrite → 5-[4-(benzyloxy)phenyl]-1-(4-methoxyphenyl)-3-(methylthio)-1H-pyrazole

HRID 351274Notes

Reaction equation

HRID 351274 reaction equation
N(OC(C)(C)C)=O.[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:26]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[N:25]=[C:24](N)[CH:23]=2)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:36][S:37]SC>C(Cl)(Cl)Cl>[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:26]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[N:25]=[C:24]([S:37][CH3:36])[CH:23]=2)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitrite2×HCID 12232Dimethyl DisulfideHCID 210909885-[4-(Benzyloxy)phenyl]-1-(4-methoxyphenyl)-1H-pyrazol-3-amine

Product 1

HCID 210909905-[4-(benzyloxy)phenyl]-1-(4-methoxyphenyl)-3-(methylthio)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of t-butyl nitrite (1.14 ml) in CHCl3 (3 ml) was added dropwise to a solution of 5-[4-(benzyloxy)phenyl]-1-(4-methoxyphenyl)-3-amino-1H-pyrazole (1.5 g) and dimethyldisulfide (1.15 ml) in CHCl3 (10 ml). After all of t-butyl nitrite solution was added, the temperature of reaction mixture began to rise and reached to reflux. After the reflux ceased, the mixture was stirred at ambient temperature for 1 hour. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography eluted with AcOEt/n-hexane=25% to give 5-[4-(benzyloxy)phenyl]-1-(4-methoxyphenyl)-3-(methylthio)-1-H-pyrazole (635.2 mg) as an oil.

Workup

  1. customthe temperature of reaction mixture
  2. temperatureto reflux
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was purified by silica gel column chromatography
  5. washeluted with AcOEt/n-hexane=25%

Sources & evidence

ORD record
ord-553cb5dc52674f219626884a42b7e015
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

Loading…