Hydrochloric Acid → 6-Aza-2-thiothymine

HRID 240268Notes

Reaction equation

HRID 240268 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[C:7]([NH:10][N:11]=[C:12]([CH3:16])[C:13](O)=[O:14])(=[S:9])[NH2:8].Cl>O>[CH3:16][C:12]1[C:13](=[O:14])[NH:8][C:7](=[S:9])[NH:10][N:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 12715712-(2-Carbamothioylhydrazono)propanoic acid

Product 1

HCID 12636666-Aza-2-thiothymine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of Na2CO3 (4.84 g, 45.6 mmol) in water (300 mL) was added 2-(2-carbamothioylhydrazono)propanoic acid (3, 7.35 g, 45.6 mmol). The mixture was heated at refluxing temperature for 3.5 h. After cooling to room temperature, the clear solution was acidified with 2 N HCl to pH ˜5. The mixture was extracted with EtOAc (60 mL×4) and CH2Cl2 (60 mL×4). The combined extracts were dried over Na2SO4 and concentrated to give 6-methyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one (4) as a white solid. MS: m/z, 144 (100%, M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat refluxing temperature for 3.5 h
  3. extractionThe mixture was extracted with EtOAc (60 mL×4) and CH2Cl2 (60 mL×4)
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a2ee18f9f2b840e988cadb8036fc0568
Source dataset
uspto-grants-2014_02
Patent number
US08648073B2

Reaction notes

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