4-Toluenesulfonyl chloride → HCID 67620835, compound

HRID 481312Notes

Reaction equation

HRID 481312 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[N+:13]([O-])[CH:14]=[CH:15][C:16]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S([Cl:28])(=O)=O)=CC=1>O1CCOCC1>[ClH:28].[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[CH2:17][Cl:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 53818160HCID 53818160, compound

Product 1

HCID 67620835HCID 67620835, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of the title compound of Preparation 7 (1.8 g, 7.3 mmol), p-toluenesulfonylchloride (2.0 g, 11 mmol) and dioxane (10 ml) was heated under reflux for 1.5 hours. The reaction mixutre was cooled to 0° C., diluted with water, treated with solid NaHCO3 and extracted with diethyl ether. The ether extracts were combined, dried (Na2 SO4), filtered and treated with HCl gas. The precipitate was filtered and washed with diethyl ether to afford 1.4 g of the title compound of this preparation. mp 149°-151° C. 1H NMR (CDCl3): δ 5.27 (2H, s), 5.42 (2H, s), 7.32-7.39 (5H, m), 8.35 (1H, d, J=6), 8.91 (1H, d, J=6), 9.28 (1H, s).

Sources & evidence

ORD record
ord-bd0ae2341e5c4d298a4fdb2a25dbb2fc
Source dataset
uspto-grants-1998_08
Patent number
US05789408

Reaction notes

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