Dimethyl Sulfoxide → 4-(6-Benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclohexanone

HRID 1257758Notes

Reaction equation

HRID 1257758 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([S:17]([N:20]2[CH:31]=[CH:30][C:29]3[C:21]2=[N:22][CH:23]=[C:24]2[C:28]=3[N:27]([CH:32]3[CH2:37][CH2:36][CH:35]([OH:38])[CH2:34][CH2:33]3)[N:26]=[N:25]2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[C:11]1([S:17]([N:20]2[CH:31]=[CH:30][C:29]3[C:21]2=[N:22][CH:23]=[C:24]2[C:28]=3[N:27]([CH:32]3[CH2:33][CH2:34][C:35](=[O:38])[CH2:36][CH2:37]3)[N:26]=[N:25]2)(=[O:18])=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 673454584-(6-Benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclohexanol

Product 1

HCID 673431594-(6-Benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclohexanoneYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a solution of oxalyl chloride (665.5 mg, 5.24 mmol) in anhydrous dichloromethane (40 mL) was added anhydrous dimethylsulfoxide (0.44 mL, 9.12 mmol) at −78° C. under nitrogen, followed by stirring for 15 minutes. Then the reaction temperature was warmed to −20° C. and a solution of 4-(6-Benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclohexanol (750 mg, 1.94 mmol) in anhydrous dichloromethane (10 mL)was added dropwise. The mixture was stirred at −20° C. for 15 minutes and warmed to room temperature. Triethylamine (2.15 g, 19.4 mmol) was added and the mixture was stirred for 90 minutes. The reaction mixture was quenched with water and extracted with ethyl acetate. The extracts were dried over sodium sulfate and concentrated under reduced pressure to give the crude product, which was crystallized form ethanol to give 600 mg (78%) of 4-(6-Benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclohexanone as a solid. 1H NMR (400 MHz, CDCl3) δ: 9.29 (s, 1H), 8.24-8.22 (m, 3H), 7.81-7.64 (m, 4H), 5.67-5.65 (m, 1H), 2.91-2.83 (m, 2H), 2.52-2.49 (m, 6H),

Workup

  1. stirringThe mixture was stirred at −20° C. for 15 minutes
  2. temperaturewarmed to room temperature
  3. stirringthe mixture was stirred for 90 minutes
  4. customThe reaction mixture was quenched with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extracts were dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product, which
  9. customwas crystallized form ethanol

Sources & evidence

ORD record
ord-258aaff01879496694e770010a859b3a
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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