Diisopropylethylamine → 4-Methyl-3-(4-methyloxazol-5-yl)-1H-1,2,4-triazole-5(4H)-thione

HRID 1175179Notes

Reaction equation

HRID 1175179 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7](O)=O.[CH3:10][NH:11][C:12](=[S:15])[NH:13][NH2:14].CCN(C(C)C)C(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C=O)C.CCOC(C)=O>[CH3:10][N:11]1[C:7]([C:6]2[O:5][CH:4]=[N:3][C:2]=2[CH3:1])=[N:14][NH:13][C:12]1=[S:15]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 2923114-Methyl-1,3-oxazole-5-carboxylic acidHCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 104202044-Methyl-3-(4-methyloxazol-5-yl)-1H-1,2,4-triazole-5(4H)-thione

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

4-Methyl-1,3-oxazole-5-carboxylic acid (commercially available) (12.9 g, 101.5 mmol) was dissolved in DMF (60 mL) and treated with 4-methyl-3-thiosemicarbazide (11.61 g, 1.10 eq). Then DIPEA (31.0 mL, 1.75 eq) was added at 20° C. Under ice bath cooling, T3P 50% w/w in EtOAc (90 mL) was added dropwise, maintaining the temperature below 15° C. over 20 minutes. The resulting mixture was then stirred at 20° C. for 6 hours.

Workup

  1. temperatureUnder ice bath cooling
  2. temperaturemaintaining the temperature below 15° C. over 20 minutes

Sources & evidence

ORD record
ord-3f37ae6c64994404b29c7781f466f170
Source dataset
uspto-grants-2010_11
Patent number
US07838680B2

Reaction notes

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