Dimethylamine → 8-hydroxy-N,N-dimethyl-1-naphthalenesulfonamide

HRID 1074418Notes

Reaction equation

HRID 1074418 reaction equation
[CH3:1][NH:2][CH3:3].[CH:4]1[CH:9]=[C:8]2[O:10][S:11]([C:14]3=[CH:15][CH:16]=[CH:17][C:6](=[C:7]23)[CH:5]=1)(=[O:13])=[O:12]>>[OH:10][C:8]1[CH:9]=[CH:4][CH:5]=[C:6]2[C:7]=1[C:14]([S:11]([N:2]([CH3:3])[CH3:1])(=[O:13])=[O:12])=[CH:15][CH:16]=[CH:17]2

Participants

3

Reactant 2

HCID 674DimethylamineHCID 657441,8-Naphthosultone

Product 1

HCID 131802708-hydroxy-N,N-dimethyl-1-naphthalenesulfonamide

Procedure

Dry dimethylamine gas was passed through a solution of 1,8-naphthasultone [5.0 g, 24 mmoles, described by I. Hideo, Japanese Patent 4927, Aug. 31, 1951; Chem. Abstr., 47, 9364b (1953)] for 1.5 hr at 20°-22° C. The mixture was stirred for 20 hr. The resulting yellow crystals were collected by filtration. The filtrate was concentrated to give more crystals. The two batches of crystals were combined giving 5 g of 8-hydroxy-N,N-dimethyl-1-naphthalenesulfonamide; mp 95° C.; NMR (CDCl3) δ 2.88 (s, 6H), 7.1-8.3 (m, 6H).

Workup

  1. filtrationThe resulting yellow crystals were collected by filtration
  2. concentrationThe filtrate was concentrated
  3. customto give more crystals

Sources & evidence

ORD record
ord-00eaaa58bea74c318b1d47f5c5a6fbf8
Source dataset
uspto-grants-1983_07
Patent number
US04391816

Reaction notes

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