Acetic Anhydride → HCID 53787295, compound

HRID 465353Notes

Reaction equation

HRID 465353 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.[C:22](OC(=O)C)(=[O:24])[CH3:23].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[C:22]([N:10]1[CH2:11][CH2:12][CH2:13][C:14]2[N:15]=[C:7]([CH:6]=[CH:5][C:4]3[CH:16]=[CH:17][CH:18]=[C:19]([O:20][CH3:21])[C:3]=3[O:2][CH3:1])[S:8][C:9]1=2)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 53812483HCID 53812483, compound

Product 1

HCID 53787295HCID 53787295, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

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 acetic anhydride (0.68 g, 6.6 mmole) with ice-cooling. The reaction mixture was heated with stirring at 80° C. 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 then recrystallized from hexane-ethyl acetate to obtain the title compound (867 mg, yield: 76.0%).

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-b9ce3eb614154a0da8a0cf62b8101592
Source dataset
uspto-grants-1992_10
Patent number
US05153201

Reaction notes

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