Hydrogen Peroxide → HCID 22048190, compound

HRID 1830849Notes

Reaction equation

HRID 1830849 reaction equation
CN1CCCC1=[O:7].[Cl:8][C:9]1[C:10]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)=[C:11]2[C:29]3[CH2:30][CH2:31][S:32][CH2:33][C:28]=3[S:27][C:12]2=[N:13][C:14]=1[CH2:15][N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:26].OO.S([O-])([O-])(=O)=S.[Na+].[Na+]>O>[Cl:8][C:9]1[C:10]([C:34]2[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=2)=[C:11]2[C:29]3[CH2:30][CH2:31][S:32](=[O:7])[CH2:33][C:28]=3[S:27][C:12]2=[N:13][C:14]=1[CH2:15][N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:26]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 13387N-methyl-2-pyrrolidoneHCID 24477Sodium ThiosulfateHCID 22048213HCID 22048213, compound

Product 1

HCID 22048190HCID 22048190, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To N-methylpyrrolidone (140.56 L) was added 2-{[3-chloro-4-(4-methoxyphenyl)-5,8-dihydro-6H-thiopyrano-[4′,3′:4,5]thieno[2,3-b]pyridin-2-yl]methyl}-1H-isoindole-1,3(2H)-dione (14.056 kg) and the mixture was dissolved by heating at about 40° C. Then, vanadium (IV) oxyacetylacetone (49.09 g) was added thereto and the 30% hydrogen peroxide was added dropwise, while maintaining at 20 to 23° C. The mixture was stirred at the same temperature for 1 hour and then cooled to 3° C., followed by adding dropwise 0.5 N sodium thiosulfate (5 L) and then water (281.14 L). The mixture was stirred for 1 hour under ice-cooling. The crystals deposited was filtered off, dried and dissolved in N-methylpyrrolidone (135.65 L). Active carbon (678 g) was added and the mixture was stirred at room temperature for 30 minutes. The active carbon was filtered off and washed with N-methylpyrrolidone (13.565 L). The filtrate and washings were combined and to the mixture was added dropwise isopropyl ether (298.43 L). The crystals deposited were filtered off, washed with isopropyl ether (67.83 L×2) to obtain the titled compound (9.56 kg, 64.3%). 1H-NMR (CDCl)δ: 2.01–2.19 (1H, m), 2.54–2.73 (2H, m), 3.00–3.07 (1H, m), 3.89 (3H, s), 3.95 (1H, d, J=16.9 Hz), 4.05 (1H, d, J=16.9 Hz), 5.20 (2H, s), 6.99–7.03 (2H, m), 7.16–7.20 (2H, m), 7.76–7.80 (2H, m), 7.91–7.95 (2H, m)

Workup

  1. dissolutionthe mixture was dissolved
  2. temperaturewhile maintaining at 20 to 23° C
  3. temperaturecooled to 3° C.
  4. stirringThe mixture was stirred for 1 hour under ice-
  5. temperaturecooling
  6. filtrationThe crystals deposited was filtered off
  7. customdried
  8. dissolutiondissolved in N-methylpyrrolidone (135.65 L)
  9. additionActive carbon (678 g) was added
  10. stirringthe mixture was stirred at room temperature for 30 minutes
  11. filtrationThe active carbon was filtered off
  12. washwashed with N-methylpyrrolidone (13.565 L)
  13. additionwas added dropwise isopropyl ether (298.43 L)
  14. filtrationThe crystals deposited were filtered off
  15. washwashed with isopropyl ether (67.83 L×2)

Sources & evidence

ORD record
ord-10c3be2ea6a44ebe8754b54f6ad510e9
Source dataset
uspto-grants-2006_06
Patent number
US07067527B2

Reaction notes

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