Acetaminophen → N-[4-(3-Amino-4-nitrophenoxy)phenyl]acetamide

HRID 1795867Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].OC1C=CC(S[C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[C:22]([NH2:29])[CH:21]=2)=CC=1.[H-].[Na+]>>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[C:22]([NH2:29])[CH:21]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

Reactant 3

HCID 1983Acetaminophen

HCID 24758Sodium hydride

HCID 221806834-(4-Hydroxyphenylsulphanyl)-2-amino-nitrobenzene

Product 1

HCID 13705240N-[4-(3-Amino-4-nitrophenoxy)phenyl]acetamide

Procedure

4-(4-Acetylaminophenoxy)-2-amino-nitrobenzene (46.57 g) was prepared from 4-acetylaminophenol (30.2 g; 0.2 mol) using the general method described for 4-(4-hydroxyphenylsulphanyl)-2-amino-nitrobenzene in Example 2, except that one equivalent of NaH was used.

Sources & evidence

ORD record: ord-40c96a8e143b487dbd6ff38eb3453fdd
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030123B2

Reaction notes

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