Ethanol → HCID 20371212, compound

HRID 616135Notes

Reaction equation

HRID 616135 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(O)C.[OH-].[Na+].[CH2:17](Br)[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19]>O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 702EthanolHCID 6259Phenacyl bromideHCID 14798Sodium HydroxideHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 20371212HCID 20371212, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.0 G. 1-amino-4-hydroxy-2-nitrobenzene in 80 ml. aqueous ethanol, containing 0.80 g. sodium hydroxide, is reacted with 4.0 g. phenacyl bromide on a steam bath under nitrogen atmosphere for 2 hours, water is added and the product collected by filtration to afford 1-amino-2-nitro-4-phenacyloxybenzene. This latter compound is hydrogenated at one atmosphere pressure in 150 ml. methanol in the presence of hydrochloric acid and 2.0 g. palladized charcoal until the theoretical uptake of hydrogen has occurred. The catalyst is filtered off and the solution stripped uner vacuum to afford 1,2-diamino-4-[1-(2-hydroxy-2-phenyl)ethoxy]benzene. This latter compound is treated overnight at room temperature with 12 g. methoxy carbonyl isothiocyanate in 120 ml. acetone. The solution is evaporated and the residue triturated with water. Recrystallization from methanol yields 1,2-bis(3-methoxycarbonyl-2-thioureido)-4-[1-(2-hydroxy-2-phenyl)ethoxy]benzene.

Workup

  1. filtrationthe product collected by filtration

Sources & evidence

ORD record
ord-bc65f036d70d46c48708d4262739c77f
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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