Dimethyl Sulfoxide → HCID 21891617, compound

HRID 720359Notes

Reaction equation

HRID 720359 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C:13]1[S:14][C:15]2[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[C:19]([O:26][CH3:27])=[CH:18][C:16]=2[N:17]=1.[Cl-].[NH4+]>ClCCl.C(N(CC)CC)C>[CH3:27][O:26][C:19]1[C:20]([O:24][CH3:25])=[C:21]([O:22][CH3:23])[C:15]2[S:14][C:13]([CH:12]=[O:11])=[N:17][C:16]=2[CH:18]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 21891577HCID 21891577, compound

Product 1

HCID 21891617HCID 21891617, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

Oxalyl chloride (0.78 mL) was dissolved in dichloromethane (10 mL), DMSO (1.49 mL) was added dropwise at −78° C., and the mixture was stirred for 30 minutes. After a solution of 2-hydroxymethyl-5,6,7-trimethoxy-benzothiazole (1.53 g) in dichloromethane (10 mL) was added dropwise at −78° C. to the mixture, stirring was conducted for 1 hour, triethylamine (6.46 mL) was added, and the resultant mixture was warmed to room temperature. After an aqueous solution of ammonium chloride was added to the mixture, extraction was conducted with dichloromethane. The resultant organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9) to obtain the title compound.

Workup

  1. stirringstirring
  2. waitwas conducted for 1 hour
  3. washThe resultant organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9)

Sources & evidence

ORD record
ord-06e16f03b44f47c4aa183ab6b5965021
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

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