Methanesulfonyl chloride → HCID 53812316, compound

HRID 465354Notes

Reaction equation

HRID 465354 reaction equation
[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:4]=1[CH:5]=[CH:6][C:7]1[S:8][C:9]2[NH:10][CH2:11][CH2:12][CH2:13][C:14]=2[N:15]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:4]=1[CH:5]=[CH:6][C:7]1[S:8][C:9]2[N:10]([S:23]([CH3:22])(=[O:25])=[O:24])[CH2:11][CH2:12][CH2:13][C:14]=2[N:15]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 53812483HCID 53812483, compound

Product 1

HCID 53812316HCID 53812316, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-(2,3-dimethoxystyryl)-4,5,6,7-tetrahydrothiazolo[5,4-b]pyridine (1.0 g, 3.3 mmole) in pyridine (10 ml) was added dropwise methanesulfonyl chloride (0.45 g, 3.97 mmole) with ice-cooling. The reaction mixture was heated with stirring at room temperature for 3 hours and then a sodium bicarbonate solution was added to the mixture which was extracted with a chloroform-methanol mixed solvent. The extract was dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography and recrystallized from hexane-ethyl acetate to obtain the title compound (1.09 g, yield: 92.7%).

Workup

  1. temperaturecooling
  2. temperatureThe reaction mixture was heated
  3. extractionwas extracted with a chloroform-methanol mixed solvent
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography
  7. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-f1eb521d514a40c2b8c832b6c75982f2
Source dataset
uspto-grants-1992_10
Patent number
US05153201

Reaction notes

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