[1]benzothiolo[3,2-d]triazin-4-ylhydrazine → HCID 12269874, compound

HRID 328675Notes

Reaction equation

HRID 328675 reaction equation
N([C:3]1[C:4]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:5]=2[N:6]=[N:7][N:8]=1)N>O>[N:6]1[C:5]2[C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][C:4]=2[CH:3]=[N:8][N:7]=1

Participants

3

Reactant 1

HCID 323432[1]benzothiolo[3,2-d]triazin-4-ylhydrazine

Product 1

HCID 12269874HCID 12269874, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2.1 g. portion of the 4-hydrazino product of Example 5 was suspended in 130 ml. of water containing 5.4 g. of mercuric oxide and the mixture was stirred at reflux temperature for 4 hours. The mixture was then cooled and filtered, and the solids were triturated with hot ethyl acetate. After filtration, the filtrate was evaporated under vacuum. The residue was redissolved in ethyl acetate-hexane and was chromatographed over a silica gel column with 1:1 ethyl acetate-hexane as the eluant. The second product off the column was the desired product, which was recrystallized from denatured ethanol-water. The yield was 1.0 g. of [1]benzothieno[3,2-d]-v-triazine, m.p. 190°-191° C.

Workup

  1. temperatureat reflux temperature for 4 hours
  2. temperatureThe mixture was then cooled
  3. filtrationfiltered
  4. customthe solids were triturated with hot ethyl acetate
  5. filtrationAfter filtration
  6. customthe filtrate was evaporated under vacuum
  7. dissolutionThe residue was redissolved in ethyl acetate-hexane
  8. customwas chromatographed over a silica gel column with 1:1 ethyl acetate-hexane as the eluant
  9. customwas recrystallized from denatured ethanol-water

Sources & evidence

ORD record
ord-7489a842ce2743f1ba71f31bdd789d2c
Source dataset
uspto-grants-1977_04
Patent number
US04018768

Reaction notes

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