Hydrochloric Acid → 2-Methylbenzenesulfonic acid

HRID 370007Notes

Reaction equation

HRID 370007 reaction equation
N#[C-].N[C:4]1[CH:12]=[CH:11][C:7]([C:8](N)=N)=[CH:6][CH:5]=1.Cl.[S:14](=O)(=[O:17])([OH:16])[OH:15].B(F)(F)F.CCOCC>O.C(O)(C)C.O1CCCC1.O1CCOCC1.C(O)C.CO>[C:7]1([CH3:8])[C:6]([S:14]([OH:17])(=[O:16])=[O:15])=[CH:5][CH:4]=[CH:12][CH:11]=1

Participants

12

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 1725p-AminobenzamidineHCID 5975CyanideHCID 8000Boron trifluoride etherate

Product 1

HCID 69252-Methylbenzenesulfonic acid

Reagents, catalysts & solvents 6

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 3776IsopropanolSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

The reaction of a substituted benzaldehyde of the formula II, an isonitrile of the formula RNC and a 4-aminobenzamidine of the formula III is advantageously carried out in a solvent (e.g. methanol, isopropanol, ethanol, dioxane, or tetrahydrofuran), or in a solvent mixture (e.g. tetrahydrofuran and water or isopropanol and water), advantageously by using an inorganic acid (e.g. hydrochloric acid, sulphuric acid or boron trifluoride etherate), or an organic acid (e.g. toluenesulphonic acid), or in acidic ion exchanger (e.g. Amberlyst K10) as catalyst, at a temperature between 0° C. and 100° C., giving compounds of the formula I. The reaction of a substituted aldehyde of the formula II, of an isonitrile of the formula R1NC and 4-aminobenzonitrile under similar reaction conditions leads to compounds of the formula IV in which Q is hydrogen.

Sources & evidence

ORD record
ord-ad53b657205646afaa67ccde8672ba4f
Source dataset
uspto-grants-2000_10
Patent number
US06140353

Reaction notes

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