4-Toluenesulfonyl chloride → HCID 13772004, compound

HRID 980835Notes

Reaction equation

HRID 980835 reaction equation
[N+:1]1([O-])[CH:6]=[CH:5][CH:4]=[C:3]2[CH:7]=[CH:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11](=[O:12])[C:2]=12.S(Cl)(C1C=CC(C)=CC=1)(=O)=[O:19].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[O:12]=[C:11]1[C:2]2[NH:1][C:6](=[O:19])[CH:5]=[CH:4][C:3]=2[CH:7]=[CH:8][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]1=2

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 54117372HCID 54117372, compound

Product 1

HCID 13772004HCID 13772004, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 0.75 gram (0.0034 mole) of the N-oxide thus obtained and 0.77 gram (0.0043 mole) of tosyl chloride in 37.5 milliliters of chloroform was added a solution of 0.58 gram (0.0042.mole) of potassium carbonate in 5.8 milliliters of water and the resulting mixture was stirred vigorously at room temperature for about 60 hours. At the end of this time the reaction mixture was washed with 10 percent aqueous sodium hydroxide whereupon a solid precipitated in the chloroform phase. The solid was recovered by filtration and recrystallized from isopropyl alcohol/methanol to obtain purified 1-oxo-benzo[5,6]cyclohepta[1,2-b]pyrid-2(1H)one product, m.p. 195°-196° C. The elemental analyses were as follows:

Workup

  1. washAt the end of this time the reaction mixture was washed with 10 percent aqueous sodium hydroxide whereupon a solid
  2. customprecipitated in the chloroform phase
  3. filtrationThe solid was recovered by filtration
  4. customrecrystallized from isopropyl alcohol/methanol
  5. customto obtain
  6. custompurified 1-oxo-benzo[5,6]cyclohepta[1,2-b]pyrid-2(1H)one product, m.p. 195°-196° C

Sources & evidence

ORD record
ord-c0d115e168cb46fdb208f80ebd1e9bd0
Source dataset
uspto-grants-1987_01
Patent number
US04639457

Reaction notes

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