Hydrochloric Acid → HCID 19832753, compound

HRID 2232041Notes

Reaction equation

HRID 2232041 reaction equation
Cl.N[C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[C:5]([C:14]2[N:15]=[N:16][N:17]([CH3:19])[N:18]=2)[CH:4]=1.[N:20]([O-])=O.[Na+].[S:24](=[O:26])=[O:25]>O.C(O)(=O)C.C(O)=O>[CH3:19][N:17]1[N:16]=[N:15][C:14]([C:5]2[CH:4]=[C:3]([S:24]([NH2:20])(=[O:26])=[O:25])[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:6]=2)=[N:18]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 19832751HCID 19832751, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19832753HCID 19832753, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 284Formic AcidSolventHCID 962WaterSolvent2×

Procedure

To a mixture of 3.1 mL of 12N hydrochloric acid, 12.5 mL of acetic acid, 3.7 mL of formic acid and 4.5 g of 5-amino-1-phenyl-3-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole was added dropwise 1.4 g of sodium nitrite in 2.5 mL of water at -8° to -6° C. The mixture was stirred for 15 minutes and then added to 20 mL of acetic acid containing 3.7 mL (liquid) of sulfur dioxide and 0.75 g of cupric chloride dihydrate. After stirring for thirty minutes and allowing to warm to room temperature, the mixture was poured into an ice and water mixture and the precipitate removed by filtration. After washing with water the solid was dissolved in tetrahydrofuran, cooled to -78° C., and ammonia (liquified, 1.0 mL) was added dropwise. The mixture was allowed to stand overnight at ambient temperature and filtered to yield a brown solid. This solid showed peaks at 3300 and 3200 cm-1, consistent for NH2, and 1370, 1185 and 1170 cm-1, consistent for SO2.

Workup

  1. stirringAfter stirring for thirty minutes
  2. customthe precipitate removed by filtration
  3. washAfter washing with water the solid
  4. dissolutionwas dissolved in tetrahydrofuran
  5. temperaturecooled to -78° C.
  6. additionammonia (liquified, 1.0 mL) was added dropwise
  7. waitto stand overnight at ambient temperature
  8. filtrationfiltered
  9. customto yield a brown solid

Sources & evidence

ORD record
ord-ed5dc02ff52f46e7806d39e17b170fa8
Source dataset
uspto-grants-1988_11
Patent number
US04786311

Reaction notes

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