HCID 18408501, compound → HCID 18408502, compound

HRID 992993Notes

Reaction equation

HRID 992993 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=2)[S:6][CH:7]=1>CS(C)=O.C(N(CC)CC)C.C(OCC)(=O)C>[CH3:19][O:18][C:10]1[CH:9]=[C:8]([C:5]2[S:6][CH:7]=[C:3]([CH:2]=[O:1])[N:4]=2)[CH:13]=[C:12]([O:14][CH3:15])[C:11]=1[O:16][CH3:17]

Participants

5

Reactant 1

HCID 18408501HCID 18408501, compound

Product 1

HCID 18408502HCID 18408502, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxymethyl-2-(3,4,5-trimethoxyphenyl)thiazole (1.53 g) was dissolved in a mixed solvent of DMSO (5 mL) and triethylamine (2.3 mL), and sulfur trioxide pyridine complex (98%, 3.09 g) was added portionwise to the solution at room temperature. After 1 hour, the reaction mixture was diluted with ethyl acetate, washed with water and saturated brine and dried over anhydrous sodium sulfate. After concentrating the reaction mixture under reduced pressure, the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1 to 1:2) to obtain the title compound.

Workup

  1. additionwas added portionwise to the solution at room temperature
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationAfter concentrating the reaction mixture under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1 to 1:2)

Sources & evidence

ORD record
ord-1a288c7dbe3041a2a3d1430f9432c02b
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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