2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 136355216, compound

HRID 2388574Notes

Reaction equation

HRID 2388574 reaction equation
[Si:1]([O:8][C@@H:9]([CH3:43])[C@@H:10]([NH:32][C:33]1[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[C:35]([Cl:41])[C:34]=1[CH3:42])[C:11]1[O:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22]CC3C=CC(OC)=CC=3)=[CH:18][CH:17]=2)=[N:14][N:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Cl)Cl.O.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Si:1]([O:8][C@@H:9]([CH3:43])[C@@H:10]([NH:32][C:33]1[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[C:35]([Cl:41])[C:34]=1[CH3:42])[C:11]1[O:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[N:14][N:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 516892Sodium BicarbonateHCID 21908982Water methylene chlorideHCID 68549795HCID 68549795, compound

Product 1

HCID 136355216HCID 136355216, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 250 mL round bottomed flask was charged with 4-((1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(5-(4-(4-methoxybenzyloxy)phenyl)-1,3,4-oxadiazol-2-yl)propylamino)-2-chloro-3-methylbenzonitrile (1.76 g, 2.84 mmol), methylene chloride —H2O (20:1, 80 mL) and 2,3-Dichloro-5,6-Dicyanobenzoquinone (3.87 g, 17.05 mmol). The reaction mixture was stirred at room temperature for 36 h and a saturated aqueous solution of sodium hydrogen carbonate (30 mL) was added followed by methylene chloride (70 mL). The phases were partitioned and the aqueous phase extracted with methylene chloride (60 mL) (×3). The combined organic extracts were dried (Na2SO4) and concentrated to furnish a white solid (1.33 g, 91%). 1H NMR (500 MHz, acetone d6, δ in ppm) δ 9.17 (br s, 1H), 7.85 (d, J=9 Hz, 2H), 7.47 (d, J=9 Hz, 1H), 6.99 (d, J=9 Hz, 2H), 6.84 (d, J=9 Hz, 1H), 6.65 (d, J=9 Hz, 1H), 5.52 (d, J=9 Hz), 5.18 (dd, J=2 and 9 Hz, 1H), 4.74-4.68 (m, 1H), 2.41 (s, 3H), 1.46 (d, J=6 Hz, 3H), 0.86 (s, 9H), 0.1 (s, 3H) and −0.35 (s, 3H).

Workup

  1. customThe phases were partitioned
  2. extractionthe aqueous phase extracted with methylene chloride (60 mL) (×3)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5a390a1f6eba4743937f953c9d783a9c
Source dataset
uspto-grants-2012_09
Patent number
US08268872B2

Reaction notes

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