Water → HCID 21717734, compound

HRID 1386924Notes

Reaction equation

HRID 1386924 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[NH:13][N:12]=2)[CH:8]=[CH:9][CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.[ClH:44].CCOCC>C(#N)C>[ClH:44].[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:14]2[NH:13][N:12]=[C:11]([C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=3)[CH2:4][NH2:1])[N:15]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 10953452Ether hydrochlorideHCID 21180317HCID 21180317, compound

Product 1

HCID 21717734HCID 21717734, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-(3-azidomethyl-phenyl)-5-(4-methoxy-phenyl)-1H-[1,2,4]triazole (980 mg, 3.2 mmol) in acetonitrile (40 ml) was treated with triphenyl phosphine (839 mg, 3.2 mmol) and water (288 mg, 16 mmol) at 20° C. for 20 min, then for 30 min. at 60° C. Upon cooling the product mixture was filtered, the solvent was evaporated and the residue chromatographed over 20 g SiO2 (Merck 230-400 mesh) with CH2Cl2-MeOH (2M NH3) 97:3 affording a solid after evaporation of the solvent. This material was dissolved in ethanol at r.t. and an excess 2N HCl/ether solution (2.0 ml, 4 mmol) was added. After 30 min. the precipitate was filtered off, washed with ether and dried under high vacuum at 60° C. overnight affording the title compound (700 mg, 69% yield) as a white solid. MS: m/e=281.3 (M+H+).

Workup

  1. temperatureUpon cooling the product mixture
  2. filtrationwas filtered
  3. customthe solvent was evaporated
  4. customthe residue chromatographed over 20 g SiO2 (Merck 230-400 mesh) with CH2Cl2-MeOH (2M NH3) 97:3 affording a solid
  5. customafter evaporation of the solvent
  6. dissolutionThis material was dissolved in ethanol at r.t.
  7. filtrationAfter 30 min. the precipitate was filtered off
  8. washwashed with ether
  9. customdried under high vacuum at 60° C. overnight

Sources & evidence

ORD record
ord-bf82a455865e4af9aa730f4f118e7147
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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