Hydrogen Peroxide → HCID 10205730, compound

HRID 1830852Notes

Reaction equation

HRID 1830852 reaction equation
[Cl:1][C:2]1[C:3]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[C:4]2[C:18]3[CH2:19][CH2:20][S:21][CH2:22][C:17]=3[S:16][C:5]2=[N:6][C:7]=1[CH2:8][N:9]1[C:13](=[O:14])[CH2:12][CH2:11][C:10]1=[O:15].CN(C)C=[O:34].OO.S([O-])([O-])(=O)=S.[Na+].[Na+]>O>[Cl:1][C:2]1[C:3]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)=[C:4]2[C:18]3[CH2:19][CH2:20][S:21](=[O:34])[CH2:22][C:17]=3[S:16][C:5]2=[N:6][C:7]=1[CH2:8][N:9]1[C:10](=[O:15])[CH2:11][CH2:12][C:13]1=[O:14]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 6228DimethylformamideHCID 24477Sodium ThiosulfateHCID 22048195HCID 22048195, compound

Product 1

HCID 10205730HCID 10205730, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-7 °C

Procedure

A mixture of 1-{[3-chloro-4-(4-methoxyphenyl)-5,8-dihydro-6H-thiopyrano[4′,3′:4,5]thieno[2,3-b]pyridin-2-yl]methyl}-2,5-pyrrolidinedione (239.6 g) and dimethylformamide (1.8 L) was cooled to −7° C. and vanadium (IV) oxyacetylacetone (691 mg) was added thereto. 30% Hydrogen peroxide (59.2 g) was added dropwise and the mixture was stirred at 2° C. or lower for 8 hours. 0.5N Sodium thiosulfate (100 ml) and water (3 L) were added dropwise at 5 to 7° C. and the mixture was stirred at 15 to 20° C. for 1 hour. Crystals deposited were filtered off to obtain the titled compound (242 g, 97.5%). 1H-NMR (CDCl3)δ: 2.13–2.20 (1H, m), 2.54–2.73 (2H, m), 3.02–3.09 (1H, m), 3.90 (3H, s), 4.00 (1H, d, J=16.9 Hz), 4.10 (1H, d, J=16.9 Hz), 5.00 (1H, d, J=17.2 Hz), 5.06 (1H, d, J=17.2 Hz), 7.01 (2H, d, J=8.1 Hz), 7.16 (2H, d, J=8.1 Hz).

Workup

  1. stirringthe mixture was stirred at 15 to 20° C. for 1 hour
  2. filtrationCrystals deposited were filtered off

Sources & evidence

ORD record
ord-a1823eed41494a689bfeb790087416e3
Source dataset
uspto-grants-2006_06
Patent number
US07067527B2

Reaction notes

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