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

HRID 1294052Notes

Reaction equation

HRID 1294052 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+](C1C=C[C:24]([O:25]C2C=CC(N)=C([N+]([O-])=O)C=2)=[CH:23]C=1)([O-])=O.[NH2:38]C1C=CC(O)=CC=1.C([S-])#N.[K+].BrBr>>[C:24]([NH:13][C:12]1[CH:14]=[CH:15][C:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[C:17]([CH:16]=2)[NH2:38])=[CH:10][CH:11]=1)(=[O:25])[CH3:23]

Participants

6

Reactant 5

HCID 4034-AminophenolHCID 24408BromineHCID 802514-(4-Nitrophenoxy)benzenamineHCID 516872Potassium thiocyanateHCID 12032722Benzenamine, 2-nitro-4-(4-nitrophenoxy)-

Product 1

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

Procedure

Compounds of Formula I, wherein D is CH, T is CH, M is C, Q is S, and q is 0, can be prepared according to the synthetic sequence shown in Scheme 7 and further detailed in the Examples section following. 4-(4-Nitrophenoxy)aniline (2), derived from (1) and 4-aminophenol, was cyclized with KSCN and Br2 in the presence of acid to provide thiazole (3). Subsequent reaction with ClCO2Me or butylisocyante (BuNCO) to give (4), followed by reduction with SnCl2 to give (5) and finally coupling with isocyanate afforded (6).

Workup

  1. customcan be prepared

Sources & evidence

ORD record
ord-4814e6921c6e408d97e6a6e8c932b07a
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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