Water → HCID 23284511, compound

HRID 368985Notes

Reaction equation

HRID 368985 reaction equation
ClS([N:5]=[C:6]=[O:7])(=O)=O.[CH2:8]([NH:10][C:11]1[C:16]([C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=O)=[CH:15][CH:14]=[CH:13][N:12]=1)[CH3:9].O>O1CCCC1>[CH2:8]([N:10]1[C:11]2[N:12]=[CH:13][CH:14]=[CH:15][C:16]=2[C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[N:5][C:6]1=[O:7])[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 23284475HCID 23284475, compound

Product 1

HCID 23284511HCID 23284511, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Chlorosulfonyl isocyanate (0.5 ml, 5.6 mmol) was added to a solution of 2-ethylamino-3-(2-thiophenecarbonyl)pyridine (1.01 g, 4.35 mmol) in tetrahydrofuran (50 ml) under ice-cooling, followed by stirring for 30 minutes. The reaction solution was mixed with water and extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. After removing sodium sulfate by filtration, the resulting filtrate was concentrated under a reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform-ethyl acetate) and recrystallized from ethyl acetate to give 1-ethyl-4-(2-thienyl)pyrido[2,3-d]pyrimidin-2(1H)-one (613 mg, 2.38 mmol, 55%).

Workup

  1. temperaturecooling
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removing sodium sulfate
  6. filtrationby filtration
  7. concentrationthe resulting filtrate was concentrated under a reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (chloroform-ethyl acetate)
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-99c3efc80eee4bdb8f860f54dae3a034
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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