Dimethylformamide → HCID 178503370, compound

HRID 973542Notes

Reaction equation

HRID 973542 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.CN(C)C=O.O=[C:15]1[CH2:20][CH2:19][CH2:18][S:17][CH:16]1[C:21](OCC)=[O:22]>C(O)(=O)C>[CH3:8][S:7][C:4]1[N:3]=[C:2]2[NH:1][C:15]3[CH2:20][CH2:19][CH2:18][S:17][C:16]=3[C:21](=[O:22])[N:6]2[N:5]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 784713-(Methylthio)-1,2,4-triazol-5-amineHCID 12269128ethyl 3-oxotetrahydro-2H-thiopyran-2-carboxylate

Product 1

HCID 178503370HCID 178503370, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To the solution of 6.5 g (0.05 mole) of 5-amino-3-methylthio-1H-1,2,4-triazole, 2.5 ml of acetic acid and 12.5 ml of dimethylformamide 9.4 g (0.05 mole) of ethyl 3-oxo-3,4,5,6-tetrahydro-2H-thiopyrane-2-carboxylate are added and the reaction mixture is boiled for 60 minutes. The precipitated product is filtered off from the hot solution, then washed with acetic acid and i-propanol and recrystallized from dimethylformamide. Thus 6.5 g (51.1%) of 2-methylthio-5,7,8,9-tetrahydrothiopyrano[3,2-d]-1,2,4-triazolo[1,5-a]pyrimidine-5(10H)-one are obtained. M.p.: higher than 350° C.

Workup

  1. filtrationThe precipitated product is filtered off from the hot solution
  2. washwashed with acetic acid and i-propanol
  3. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-56224d54a21c4cbc816c24544ca729b0
Source dataset
uspto-grants-1991_11
Patent number
US05064826

Reaction notes

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