Ammonium Chloride → HCID 178440349, compound

HRID 1090155Notes

Reaction equation

HRID 1090155 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]#[N:23])=[CH:12][CH:11]=2)[C:7]([CH2:24][CH2:25][CH3:26])=[N:6][N:5]=1.[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH3:1][O:2][CH2:3][C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:29][N:28]=[N:27][N:23]=3)=[CH:12][CH:11]=2)[C:7]([CH2:24][CH2:25][CH3:26])=[N:6][N:5]=1

Participants

5

Reactant 3

HCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 14987345HCID 14987345, compound

Product 1

HCID 178440349HCID 178440349, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methoxymethyl-5-propyl-4-[(2'-cyanobiphenyl-4-yl)methyl]-1,2,4-triazole (1.5 g, 4.33 mmol) in DMF (35 ml) was added sodium azide (NaN3, 0.84 g, 13 mmol) and ammonium chloride (NH4Cl, 0.69 g, 13 mmol). The mixture was stirred at 100° C. for four days whereupon an additional 0.3 g NaN3 and 0.23 g NH4Cl were added. Stirring was continued 2 days further at 100° C. The solvent was removed (rotary evaporation) and the residue was partitioned between ethyl acetate and water (100 ml ea). The organic phase was dried (MgSO4), filtered and concentrated to a viscous light brown oil (1.5 g) which was purified by flash chromatography on silica gel to give 350 mg (21%) of an off-white solid; m.p. 201°-205° C. (dec.).

Workup

  1. additionwere added
  2. customThe solvent was removed
  3. custom(rotary evaporation)
  4. customthe residue was partitioned between ethyl acetate and water (100 ml ea)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to a viscous light brown oil (1.5 g) which
  8. customwas purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e90fab80d8754b869a5ef7ceb9ad6428
Source dataset
uspto-grants-1992_01
Patent number
US05081127

Reaction notes

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