2-Naphthalenecarboxamide, 4-amino-N-[4-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyl]-1-hydroxy- → 4-(3-Amino-4-hydroxybenzenesulfonamido)-1-hydroxy-N-[4-(2,4-di-tert-pentylphenoxy)butyl]-2-naphthamide

HRID 2052196Notes

Reaction equation

HRID 2052196 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([CH2:30][CH3:31])([CH3:29])[CH3:28])=[CH:23][C:22]=2[C:32]([CH2:35][CH3:36])([CH3:34])[CH3:33])=[O:14])[CH:3]=1.[OH:37][C:38]1[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][C:39]=1[N+:48]([O-])=O>>[NH2:48][C:39]1[CH:40]=[C:41]([S:44]([NH:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([OH:12])=[C:4]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([CH2:30][CH3:31])([CH3:28])[CH3:29])=[CH:23][C:22]=3[C:32]([CH2:35][CH3:36])([CH3:34])[CH3:33])=[O:14])[CH:3]=2)(=[O:46])=[O:45])[CH:42]=[CH:43][C:38]=1[OH:37]

Participants

3

Reactant 2

HCID 30848622-Naphthalenecarboxamide, 4-amino-N-[4-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyl]-1-hydroxy-HCID 36704794-Hydroxy-3-nitrobenzene-1-sulfonyl chloride

Product 1

HCID 233361094-(3-Amino-4-hydroxybenzenesulfonamido)-1-hydroxy-N-[4-(2,4-di-tert-pentylphenoxy)butyl]-2-naphthamide

Procedure

This compound was prepared in two steps by conventional procedures of the type well known in the art. 4-Amino-1-hydroxy-N-[4-(2,4-di-tert-pentylphenoxy)butyl]-2-naphthamide (U.S. Pat. No. 3,954,476, column 25) was converted to the sulfonamide by reaction with 4-hydroxy-3-nitrobenzenesulfonyl chloride. Secondly, the nitro group was reduced to the amino compound by catalytic hydrogenation.

Workup

  1. customThis compound was prepared in two steps by conventional procedures of the type

Sources & evidence

ORD record
ord-9f7c9648c71249d988851dc0114501fb
Source dataset
uspto-grants-1980_01
Patent number
US04183754

Reaction notes

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