2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 73330644, compound

HRID 517544Notes

Reaction equation

HRID 517544 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:21]2[O:22][CH2:23][CH:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:25]=2)[S:5][C:6]=1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[CH:9]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1.O=[Mn]=O>[CH3:1][C:2]1[N:3]=[C:4]([C:21]2[O:22][CH:23]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:25]=2)[S:5][C:6]=1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]2)[CH:9]=1

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86711484HCID 86711484, compound

Product 1

HCID 73330644HCID 73330644, compoundYield 5.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

To a suspension of 2-(4-methyl-5-(3-(4-methylpiperazin-1-yl)benzyl)thiazol-2-yl)-4-phenyl-4,5-dihydrooxazole (17 mg, 0.04 mmol) and MnO2 (21 mg, 0.24 mmol) in toluene (2 mL), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (5 mg, 0.02 mmol) was added. The mixture was refluxed for 48 h under N2, and then cooled. The precipitate was filtered and washed with DCM/MeOH (10/1, 30 mL). The filtrate was washed with NaHCO3 (2 M, 10 mL) and brine (10 mL), dried over Na2SO4, filtered, concentrated and purified by prep-TLC (DCM:MeOH=15:1) to afford 2-(4-methyl-5-(3-(4-methylpiperazin-1-yl)benzyl)thiazol-2-yl)-4-phenyloxazole as a light yellow solid (1.0 mg, 5%). MS (ES+) C25H26N4OS requires: 430, found: 431[M+H]+. 1H-NMR (500 MHz, CDCl3) δ ppm 7.98 (s, 1H), 7.80 (d, J=9.5 Hz, 2H), 7.41 (t, J=7.5 Hz, 2H), 7.34 (t, J=7.5 Hz, 1H), 7.22 (t, J=7.5 Hz, 1H), 6.80-6.82 (m, 1H), 6.72-6.78 (m, 2H), 4.10 (s, 2H), 3.28 (br, 4H), 2.72 (br, 4H), 2.50 (s, 3H), 2.45 (s, 3H).

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed for 48 h under N2
  3. temperaturecooled
  4. filtrationThe precipitate was filtered
  5. washwashed with DCM/MeOH (10/1, 30 mL)
  6. washThe filtrate was washed with NaHCO3 (2 M, 10 mL) and brine (10 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by prep-TLC (DCM:MeOH=15:1)

Sources & evidence

ORD record
ord-4baac913871841f791b319ca437013a5
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Reaction notes

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