Ethanol → HCID 16222810, compound

HRID 856980Notes

Reaction equation

HRID 856980 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][C:17]=3[Cl:18])[O:10][N:9]=2)=[CH:4][C:3]=1[NH2:19].[CH2:20]([OH:22])[CH3:21].C([CH2:25][C:26](OBr)=[O:27])C.C(N(CC)CC)C>C(OCC)(=O)C>[CH2:20]([O:22][C:26](=[O:27])[CH2:25][NH:19][C:3]1[CH:4]=[C:5]([C:8]2[N:12]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][C:17]=3[Cl:18])[O:10][N:9]=2)[CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:21]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 99956372-Chloro-5-[5-(3-chlorothiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenylamineHCID 23177133Bromo ethylacetate

Product 1

HCID 16222810HCID 16222810, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 10 mL microwave reaction flask reaction charged with a magnetic stir bar, was added 2-chloro-5-[5-(3-chlorothiophene-2-yl)-[1,2,4]oxadiazol-3-yl]-phenylamine (0.100 g, 0.320 mmol), anhydrous ethanol (1.3 mL), bromo ethylacetate (0.241 g, 1.44 mmol) and triethylamine (67 μL, 0.48 mmol). The suspension was reacted at 120° C., for 15 min in a microwave set at 70 watts. The resulting yellow suspension was diluted with ethyl acetate (50 mL) and the organic layer was then washed with H2O (2×15 mL), brine (10 mL), dried over MgSO4, and the solvent was removed by evaporation. The white solid was then purified by flash column chromatography (silica gel, elution with EtOAc:hexanes, 1:5) to yield 0.119 g (94%) of the title compound as a white solid. 1H NMR (CDCl3): 7.59 (dd, 1H, J=5.2 and 1.4 Hz), 7.47 (dd, 1H, J=8.3 and 1.7 Hz), 7.38 (dd, 1H, J=8.3 and 1.1 Hz), 7.27 (d, 1H, J=1.7 Hz), 7.10 (dd, 1H, J=5.2 and 1.4 Hz), 5.11 (t, 1H, J=5.0 Hz), 4.29 (q, 2H, J=7.1 Hz), 4.05 (d, 2H, J=5.2 Hz), 1.33 (t, 3H, J=7.1 Hz).

Workup

  1. customTo a 10 mL microwave reaction flask reaction
  2. additioncharged with a magnetic stir bar
  3. customThe suspension was reacted at 120° C., for 15 min in a microwave
  4. washthe organic layer was then washed with H2O (2×15 mL), brine (10 mL)
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed by evaporation
  7. customThe white solid was then purified by flash column chromatography (silica gel, elution with EtOAc:hexanes, 1:5)

Sources & evidence

ORD record
ord-39229a8998f944d3a1c196e06ac9272d
Source dataset
uspto-grants-2006_12
Patent number
US07144876B2

Reaction notes

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