Ethyl Acetate → HCID 67070507, compound

HRID 732065Notes

Reaction equation

HRID 732065 reaction equation
Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=2[F:15])[N:4]=1.[CH2:16]([N:18]1[C:22]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[N:21][NH:20][C:19]1=[S:28])[CH3:17].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[F:15][C:9]1[CH:10]=[CH:11][C:12]([F:14])=[CH:13][C:8]=1[C:5]1[N:4]=[C:3]([CH2:2][S:28][C:19]2[N:18]([CH2:16][CH3:17])[C:22]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[N:21][N:20]=2)[O:7][N:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 7365254-Ethyl-5-thiophen-2-yl-4H-[1,2,4]triazole-3-thiolHCID 67070510HCID 67070510, compound

Product 1

HCID 67070507HCID 67070507, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloromethyl-3-(2,5-difluoro-phenyl)-[1,2,4]oxadiazole (23 mg, 0.10 mmol) and 4-ethyl-5-thiophen-2-yl-2,4-dihydro-[1,2,4]triazole-3-thione (23 mg, 0.11 mmol) was dissolved in anhydrous DMF (1 ml) and potassium carbonate (21 mg, 0.15 mmol) was added. After stirring for 22 h ethyl acetate was added, the resulting mixture was washed twice with water and once with brine, dried over MgSO4 and evaporated. Flash chromatography using heptane:ethyl acetate 1:1 yielded the title compound (20 mg, 50%). 1H NMR (CDCl3) d (ppm): 7.64 (m, 1H), 7.45 (d, 1H), 7.39 (d, 1H), 7.10 (m, 3H), 4.70 (s, 2H), 4.08 (q, 2H), 1.32 (t, 3H).

Workup

  1. additionwas added
  2. washthe resulting mixture was washed twice with water and once with brine
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-9edb72b03a3a4c7b8e5e1458ac8eea0f
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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