Hydrochloric Acid → HCID 14990699, compound

HRID 2248331Notes

Reaction equation

HRID 2248331 reaction equation
CS([O-])(=O)=O.N[N:7]1[CH:11]=[N+:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=2)[N:9]=[CH:8]1.Cl.[PH2](=O)O.N([O-])=O.[Na+].[OH-].[NH4+]>O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:10]2[CH:11]=[N:7][CH:8]=[N:9]2)=[CH:14][C:15]=1[N+:20]([O-:22])=[O:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 4124402Phosphinic AcidHCID 23668193Sodium NitriteHCID 178505359HCID 178505359, compound

Product 1

HCID 14990699HCID 14990699, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 8.75 parts of 4-amino-1-[(4-chloro-3-nitrophenyl)methyl]-1,2,4-triazolium methanesulfonate in 85 parts of a hydrochloric acid solution 1N were added 7.15 parts of phosphinic acid 50%. After cooling in ice, a solution of 3.5 parts of sodium nitrite in 15 parts of water was added. The mixture was stirred for 2 hours at room temperature. An excess of concentrated ammonium hydroxide was added and stirring was continued for 15 minutes. The product was filtered off, washed with water, 2-propanol and 2,2'-oxybispropane and crystallized from 8 parts of 2-propanol. The product was filtered off and dried, yielding 5 parts (83.8%) of 1-[(4-chloro-3-nitrophenyl)methyl]-1H-1,2,4-triazole; mp. 98.9° C. (int. 143).

Workup

  1. temperatureAfter cooling in ice
  2. stirringstirring
  3. waitwas continued for 15 minutes
  4. filtrationThe product was filtered off
  5. washwashed with water, 2-propanol and 2,2'-oxybispropane
  6. customcrystallized from 8 parts of 2-propanol
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-4f5d49b88ba84f0f8ca0793e9b013c58
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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