Acetic Acid → HCID 178503365, compound

HRID 973545Notes

Reaction equation

HRID 973545 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.O=[C:10]1[CH2:15][CH2:14][S:13][CH2:12][CH:11]1[C:16](OCC)=O.C(O)(=[O:23])C>>[CH3:8][S:7][C:4]1[NH:5][N:6]2[CH2:16][C:11]3[CH2:12][S:13][CH2:14][C:15](=[O:23])[C:10]=3[N:1]=[C:2]2[N:3]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 784713-(Methylthio)-1,2,4-triazol-5-amineHCID 256936Ethyl 4-oxotetrahydro-2H-thiopyran-3-carboxylate

Product 1

HCID 178503365HCID 178503365, compoundYield 63%

Procedure

1.30 g (0.01 mole) of 5-amino-3-methylthio-1H-1,2,4-triazole are dissolved in 6 ml of acetic acid, then 1.88 g (0.01 mole) of ethyl 4-oxo-3,4,5,6-tetrahydro-2H-thiopyrane-3-carboxylate are added and the reaction mixture is boiled for 60 minutes. The precipitated product is filtered off from the hot solution and washed with i-propanol. The 1.6 g (63%) of 2-methylthio-5,6,8,9-tetrahydrothiopyrano[4,3-d]-1,2,4-triazolo[1,5-a]pyrimidine-5(10H)-one thus obtained are dissolved in 12 ml of hot 10% sodium hydroxide solution and after cooling down the precipitated 2-methylthio-5,6,8,9-tetrahydrothiopyrano[4,3-d]-1,2,4-triazolo[1,5-a]pyrimidine-5(10H)-one sodium salt is filtered off (melting point: higher than 350° C.), then dissolved in 30 ml of distilled water. Thereafter the solution is made highly acidic with the aid of acetic acid and the 2-methylthio-5,6,8,9-tetrahydrothiopyrano[4,3-d]-1,2,4-triazolo[1,5-a]pyrimidine-5(10H)-one is precipitated again.

Workup

  1. filtrationThe precipitated product is filtered off from the hot solution
  2. washwashed with i-propanol

Sources & evidence

ORD record
ord-71222a5e465e4b5bb849364ab1d6f914
Source dataset
uspto-grants-1991_11
Patent number
US05064826

Reaction notes

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