Acetic Anhydride → Benzenesulfonic acid, 5-(acetylamino)-2-amino-

HRID 2260465Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[S:9]([OH:12])(=[O:11])=[O:10].[C:13](OC(=O)C)(=[O:15])[CH3:14]>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:13](=[O:15])[CH3:14])=[CH:4][C:3]=1[S:9]([OH:12])(=[O:10])=[O:11]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 666172,5-Diaminobenzenesulfonic acid

Product 1

HCID 66788Benzenesulfonic acid, 5-(acetylamino)-2-amino-

Procedure

That is, 2,5-diaminobenzenesulfonic acid is acetylated with acetic anhydride to obtain 2-amino-5-acetylaminobenzenesulfonic acid, which is then diazotized in an ordinary manner and coupled with 2,5-xylidine to thereby obtain the compound [E] shown below.

Sources & evidence

ORD record: ord-7097993beacf41199f4937b506c14dce
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05478384

Reaction notes

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