2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 135621876, compound

HRID 982870Notes

Reaction equation

HRID 982870 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]1[S:17][CH2:16][CH2:15][N:14]=[C:13]([C:18]2[C:19](=[O:26])[O:20][C:21]([CH3:25])=[CH:22][C:23]=2[OH:24])[CH2:12]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[S:17][CH2:16][CH2:15][N:14]=[C:13]([C:18]2[C:19](=[O:26])[O:20][C:21]([CH3:25])=[CH:22][C:23]=2[OH:24])[CH:12]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 1354004393-(7-(2,4-Dimethoxyphenyl)-2,3,6,7-tetrahydro-(1,4)thiazepin-5-yl)-4-hydroxy-6-methylpyran-2-one

Product 1

HCID 135621876HCID 135621876, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

3-[7-(2,4-Dimethoxyphenyl)-2,3,6,7-tetrahydro-[1,4]thiazepin-5-yl]-4-hydroxy-6-methyl-pyran-2-one (150 mg, 0.39 mmol), prepared as in Reference 5, was dissolved in toluene (2 ml) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.3 mL, 35 wt % in water) was added to the solution. The mixture was stirred at 80° C. The reaction was monitored by analytical HPLC and after reaction was complete (20 minutes) the solvent was then removed in vacuo. Product was purified by preparative HPLC (RPC18 column, 2-80% acetonitrile/water containing 0.1% HCl) to provide 3-[7-(2,4-dimethoxy-phenyl)-2,3-dihydro-[1,4]thiazepin-5-yl]-4-hydroxy-6-methyl-pyran-2-one (35 mg) as an orange powder. LCMS: MH+ 373.0.

Workup

  1. customafter reaction
  2. custom(20 minutes)
  3. customwas then removed in vacuo
  4. customProduct was purified by preparative HPLC (RPC18 column, 2-80% acetonitrile/water containing 0.1% HCl)

Sources & evidence

ORD record
ord-adf97076cf8c426ba714eca51f9b1f46
Source dataset
uspto-grants-2005_03
Patent number
US06861419B2

Reaction notes

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