Hydrochloric Acid → HCID 178518769, compound

HRID 2254732Notes

Reaction equation

HRID 2254732 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12](=O)[C:13]([O:15]CCCCCC)=O)[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[OH:8].[NH2:23][NH:24][C:25]([NH2:27])=[S:26].[OH-].[Na+].Cl>O>[OH:1][C:2]1[CH:3]=[C:4]([C:12]2[C:13](=[O:15])[NH:27][C:25]([SH:26])=[N:24][N:23]=2)[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[OH:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723789ThiosemicarbazideHCID 5747978Benzeneacetic acid, 3,4-dihydroxy-5-nitro-alpha-oxo-, hexyl ester

Product 1

HCID 178518769HCID 178518769, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 2.05 g of n-hexyl 3,4-dihydroxy-5-nitrophenylglyoxylate and 600.8 mg of thiosemicarbazide is stirred intensively at 90° for 30 minutes. The mixture is then cooled to 40° and treated with a solution of 870.1 mg of sodium hydroxide in 15 ml of water. The solution is subsequently heated to 90° for 30 minutes, cooled to room temperature and treated dropwise with 2 ml of conc. hydrochloric acid. The crystallized-out product is filtered under suction and then dissolved in ethyl acetate. The solution is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated. There is obtained 6-(3,4-dihydroxy-5-nitrophenyl)-3-mercapto-1,2,4-triazin-5(4H)-one of m.p. 282°-284° (from ethanol).

Workup

  1. temperatureThe mixture is then cooled to 40°
  2. temperatureThe solution is subsequently heated to 90° for 30 minutes
  3. filtrationThe crystallized-out product is filtered under suction
  4. dissolutiondissolved in ethyl acetate
  5. washThe solution is washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-156ba098397942d09b234cade26ccd6f
Source dataset
uspto-grants-1993_08
Patent number
US05236952

Reaction notes

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