2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 10358327, compound

HRID 751298Notes

Reaction equation

HRID 751298 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=4)=[N:13][N:12]4[CH2:22][CH2:23][CH2:24][C:11]=34)=[CH:9][C:4]=2[CH2:3][CH2:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=4)=[N:13][N:12]4[CH2:22][CH2:23][CH2:24][C:11]=34)=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 11723355HCID 11723355, compound

Product 1

HCID 10358327HCID 10358327, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Dissolve 3-(2,3-dihydro-benzofuran-5-yl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (Example 26; 10 mg, 0.03 mmol) and 2,3-dichloro-5,6-dicyanobenzoquinone (14 mg, 0.06 mmol) in anhydrous toluene (4 mL). Heat the mixture for 6 hr at 110° C. Evaporate the solvent and purify the crude product by flash chromatography to give target compound as a pale yellow solid (9 mg, 91%). MS m/e (315.2, M+1).

Workup

  1. customEvaporate the solvent
  2. custompurify the crude product by flash chromatography

Sources & evidence

ORD record
ord-be5bbec6c8844a88aaf1d51033ed5382
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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