Sulfur Dioxide → 3-Amino-4-bromo-2,5-diisopropylbenzenesulfonamide

HRID 1973542Notes

Reaction equation

HRID 1973542 reaction equation
C(C1C=CC(C(C)C)=CC=1N)(C)C.BrC1C(C(C)C)=CC(N)=C(C(C)C)C=1.BrC1C(C(C)C)=CC(N)=C(C(C)C)C=1[N+]([O-])=O.S(=O)=O.[Br:48][C:49]1[C:54]([CH:55]([CH3:57])[CH3:56])=[CH:53][C:52]([S:58]([NH2:61])(=[O:60])=[O:59])=[C:51]([CH:62]([CH3:64])[CH3:63])[C:50]=1[N+:65]([O-])=O>>[NH2:65][C:50]1[C:51]([CH:62]([CH3:64])[CH3:63])=[C:52]([S:58]([NH2:61])(=[O:60])=[O:59])[CH:53]=[C:54]([CH:55]([CH3:57])[CH3:56])[C:49]=1[Br:48]

Participants

6

Reactant 5

HCID 1119Sulfur DioxideHCID 154426012,5-Bis(propan-2-yl)anilineHCID 214919614-Bromo-2,5-diisopropyl-3-nitrobenzenesulfonamideHCID 214920334-Bromo-2,5-diisopropyl-3-nitroanilineHCID 214921264-Bromo-2,5-diisopropylaniline

Product 1

HCID 214919323-Amino-4-bromo-2,5-diisopropylbenzenesulfonamide

Procedure

3-Amino-4-bromo-2,5-diisopropylbenzenesulfonamide is prepared by known general methods (L. F. Fieser and M. Fieser, Reinhold Publishing Corp., N. Y., 3rd ed., 1956, pgs 599-602) from 2,5-diisopropylaniline by acylation to 2,5-diisopropylacetanilide, bromination to 4-bromo-2,5-diisopropylacetanilide, hydrolysis to 4-bromo-2,5-diisopropylaniline, nitration to 4-bromo-2,5-diisopropyl-3-nitroaniline, diazotization in the presence of cuprous chloride and sulfur dioxide to 4-bromo-2,5-diisopropyl-3-nitrobenzenesulfonamide (method of Example 6) and reduction.

Sources & evidence

ORD record
ord-1941e9f06c8c450684175aba3f097cf1
Source dataset
uspto-grants-1976_12
Patent number
US03997603

Reaction notes

Loading…