Ammonium Chloride → 5-Amino-7-methyl-8-[3-(2,5-dichlorophenyl)-2-butenyl]tetrazolo[1,5-c]pyrimidine

HRID 1939666Notes

Reaction equation

HRID 1939666 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][CH:10]=[C:11]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[Cl:20])[CH3:12])=[C:4]([CH3:21])[N:3]=1.[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+]>CS(C)=O>[NH2:1][C:2]1[N:7]2[N:22]=[N:23][N:24]=[C:6]2[C:5]([CH2:9][CH:10]=[C:11]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[Cl:20])[CH3:12])=[C:4]([CH3:21])[N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 54181037HCID 54181037, compound

Product 1

HCID 536571025-Amino-7-methyl-8-[3-(2,5-dichlorophenyl)-2-butenyl]tetrazolo[1,5-c]pyrimidineYield 85.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Under a nitrogen atmosphere, a solution of 2.0 grams (0.006 mole) of 2-amino-4-chloro-6-methyl-5-[3-(2,5-dichlorophenyl)-2-butenyl]pyrimidine, 0.4 gram (0.006 mole) of sodium azide, and 0.3 gram (0.006 mole) of ammonium chloride in 15 mL of dimethyl sulfoxide is stirred at ambient temperature for about 18 hours. After this time the reaction mixture is poured into ice-water. The mixture is stirred until the ice melted, and the resultant solid is collected by filtration. The solid is dissolved in methylene chloride, and the solution is dried with magnesium sulfate. The mixture is filtered, and the filtrate is concentrated under reduced pressure to a residual solid. The solid is recrystallized from methylene chloride/petroleum ether, yielding 1.8 grams of 5-amino-7-methyl-8-[3-(2,5-dichlorophenyl)-2-butenyl]tetrazolo[1,5-c]-pyrimidine. The NMR spectrum is consistent with the proposed structure.

Workup

  1. filtrationthe resultant solid is collected by filtration
  2. dissolutionThe solid is dissolved in methylene chloride
  3. dry with materialthe solution is dried with magnesium sulfate
  4. filtrationThe mixture is filtered
  5. concentrationthe filtrate is concentrated under reduced pressure to a residual solid
  6. customThe solid is recrystallized from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-1f56af90c61348fc8e189c1d02ca7148
Source dataset
uspto-grants-1997_12
Patent number
US05696259

Reaction notes

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