Sulfuric Acid → HCID 86739755, compound

HRID 1979676Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([NH:8]C(=O)C)[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[CH:14]([OH:35])[CH2:15][S:16]([CH2:19][CH:20]([OH:34])[C:21]1[CH:26]=[C:25]([O:27][CH3:28])[C:24]([NH:29]C(=O)C)=[CH:23][C:22]=1[CH3:33])(=[O:18])=[O:17].S(=O)(=O)(O)O>>[CH3:33][C:22]1[CH:23]=[C:24]([NH2:29])[C:25]([O:27][CH3:28])=[CH:26][C:21]=1[CH:20]([OH:34])[CH2:19][S:16]([CH2:15][CH:14]([OH:35])[C:3]1[CH:4]=[C:5]([O:12][CH3:13])[C:6]([NH2:8])=[CH:7][C:2]=1[CH3:1])(=[O:18])=[O:17]

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 86739756HCID 86739756, compound

Product 1

HCID 86739755HCID 86739755, compoundYield 94%

Procedure

292.9 Parts of 2-methyl-4-acetylamino-5-methoxyphenyl-β-hydroxyethylsulfone (purity: 98%) and 500 parts of diatomaceous earth were fed into a dispersion kneader (manufactured by Inoue Seisakusho) operated at 70 r.p.m. and then 210 parts of 70% sulfuric acid (molar ratio: 1.5) were added thereto. The mixture was maintained at 95° to 100° C. under reduced pressure (300 mmHg) for 7 hours while distilling off the produced water and acetic acid. The reaction product was analyzed by liquid chromatography, obtaining 2-methyl-4-amino-5-methoxyphenyl-β-hydroxyethylsulfone in a 94% yield.

Workup

temperatureThe mixture was maintained at 95° to 100° C. under reduced pressure (300 mmHg) for 7 hours
distillationwhile distilling off the produced water and acetic acid

Sources & evidence

ORD record: ord-2b5f185d176343e6bd0b6d170f1b2456
Source dataset: uspto-grants-1984_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04482501

Reaction notes

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