4-Toluenesulfonyl chloride → HCID 13772002, compound

HRID 980833Notes

Reaction equation

HRID 980833 reaction equation
[O:1]=[C:2]1[C:12]2[C:7](=[N+:8]([O-])[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]1=2.S(Cl)(C1C=CC(C)=CC=1)(=O)=[O:19].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[O:1]=[C:2]1[C:12]2[CH:11]=[CH:10][C:9](=[O:19])[NH:8][C:7]=2[CH:6]=[CH:5][C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]1=2

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 13772001HCID 13772001, compound

Product 1

HCID 13772002HCID 13772002, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 2.23 grams (0.01 mole) of 5-oxo-benzo[4,5]cyclohepta[1,2-b]pyridine N-oxide intermediate and 2.29 grams (0.012 mole) of tosyl chloride in 100 milliliters of chloroform was added a solution of 1.76 grams of potassium carbonate in 25 milliliters of water and the resulting mixture stirred vigorously for 4 days at room temperature. During this period the desired 5-oxo-benzo[4,5]cyclohepta[1,2-b]pyrid-2(1H)one product formed in the reaction mixture as a solid. The solid was recovered by filtration, was washed successively with 10 percent sodium hydroxide solution, water and hot methanol, and was dried. The dried product was a TLC homogeneous 5-oxo-benzo-[4,5]cyclohepta[1,2-b]pyrid-2(1H)one.0.25 methanol solvate, m.p. 320° C. The elemental analyses were as follows:

Sources & evidence

ORD record
ord-f05a930be91744d286f935143c2a8e20
Source dataset
uspto-grants-1987_01
Patent number
US04639457

Reaction notes

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