Benzyl Bromide → 1-Acetamido-4-benzyloxy-2-nitrobenzene

HRID 616138Notes

Reaction equation

HRID 616138 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(C)=O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 4024832N-(4-hydroxy-2-nitrophenyl)acetamide

Product 1

HCID 2658881-Acetamido-4-benzyloxy-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.94 G. of 1-acetamido-4-hydroxy-2-nitrobenzene, 4.2 g. anhydrous potassium carbonate and 5.13 g. benzyl bromide were refluxed overnight with stirring in 100 ml. acetone. Evaporation and extraction of the residue with dichloromethane affords 1-acetamido-4-benzyloxy-2-nitrobenzene. This latter compound is treated with sodium hydroxide in methanol, warmed briefly on a steam bath for about 15 minutes until the reaction is complete, diluted with water and extracted with dichloromethane to afford 1-amino-4-benzyloxy-2-nitrobenzene. This latter compound is treated for 4 hours in a refluxing hydrochloric acid acidified mixture of 160 ml. methanol and 40 ml. water with 4 g. iron powder (added in two portions) and 1 g. ferrous sulfate. The mixture is poured into 150 ml. concentrated ammonia, then extracted with chloroform to afford 1,2-diamino-4-benzyloxybenzene. This latter compound is treated in accordance with the fourth paragraph of Example XV to afford 4 -benzyloxy-1,2-bis(3-methoxycarbonyl-2-thioureido)benzene.

Workup

  1. customEvaporation and extraction of the residue with dichloromethane

Sources & evidence

ORD record
ord-bfb28cabe45f41cf8fe9eda3f9c948d9
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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