Dimethyl Sulfoxide → HCID 22048195, compound

HRID 481131Notes

Reaction equation

HRID 481131 reaction equation
CS(C)=O.C[O-].[Na+].[C:8]1(=[O:14])[NH:12][C:11](=[O:13])[CH2:10][CH2:9]1.[Cl:15][C:16]1[C:17]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[C:18]2[C:26]3[CH2:27][CH2:28][S:29][CH2:30][C:25]=3[S:24][C:19]2=[N:20][C:21]=1[CH2:22]Cl>O.CO>[Cl:15][C:16]1[C:17]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[C:18]2[C:26]3[CH2:27][CH2:28][S:29][CH2:30][C:25]=3[S:24][C:19]2=[N:20][C:21]=1[CH2:22][N:12]1[C:11](=[O:13])[CH2:10][CH2:9][C:8]1=[O:14]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11439SuccinimideHCID 10942334Sodium MethoxideHCID 22048222HCID 22048222, compound

Product 1

HCID 22048195HCID 22048195, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To dimethyl sulfoxide (2450 ml) was added 28% sodium methoxide (97.4 g), followed by addition of succinimide (178.9 g). The mixture was stirred at about 20° C. for 30 minutes and then 3-chloro-2-chloromethyl-5,8-dihydro-4-(4-methoxyphenyl)-6H-thiopyrano[4′,3′:4,5]thieno-[2,3-b]pyridine (490 g) was added thereto. The mixture was stirred at room temperature for 2.5 hours and then a mixture of methanol (1225 ml) and water (490 g) was added dropwise thereto. The mixture was stirred at 10° C. or lower and crystals deposited were filtered off to the titled compound (546 g, 96. 3%).

Workup

  1. stirringThe mixture was stirred at room temperature for 2.5 hours
  2. additionwas added dropwise
  3. stirringThe mixture was stirred at 10° C.
  4. filtrationlower and crystals deposited were filtered off to the titled compound (546 g, 96. 3%)

Sources & evidence

ORD record
ord-3fe16100a56a43e29471550e516623df
Source dataset
uspto-grants-2003_11
Patent number
US06653476B2

Reaction notes

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