Potassium Carbonate → ethyl 2-(1-(2-cyclopropylethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylate

HRID 555004Notes

Reaction equation

HRID 555004 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[C:16](=[O:17])[NH:15][N:14]=[CH:13]2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:35][CH2:36][CH:37]2[CH2:39][CH2:38]2)(=O)=O)=CC=1>CC(C)=O>[CH:37]1([CH2:36][CH2:35][N:15]2[C:16](=[O:17])[N:12]([C:4]3[S:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([CH3:1])[N:3]=3)[CH:13]=[N:14]2)[CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13568392Toluene-4-sulfonic acid 2-cyclopropyl-ethyl esterHCID 57920013ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate

Product 1

HCID 66661569ethyl 2-(1-(2-cyclopropylethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate (0.25 g, 0.98 mmol) and potassium carbonate (0.20 g, 1.47 mmol) in acetone (20 mL) was added 2-cyclopropylethyl 4-methylbenzenesulfonate (0.28 g, 1.18 mmol). The reaction mixture was heated to reflux for 24 hours, cooled to ambient temperature and filtered. The filtrate was concentrated in vacuo to afford ethyl 2-(1-(2-cyclopropylethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylate in 63% yield (0.20 g): MS (ES+) m/z 323.3 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 24 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-37ed7e5268af497fbd4f8829196cad58
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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