Butyl bromide → 1-Acetamido-4-n-butoxy-2-nitrobenzene

HRID 616133Notes

Reaction equation

HRID 616133 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].[CH2:15](Br)[CH2:16][CH2:17][CH3:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 4024832N-(4-hydroxy-2-nitrophenyl)acetamide

Product 1

HCID 218224141-Acetamido-4-n-butoxy-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.94 G. of 1-acetamido-4-hydroxy-2-nitrobenzene, 4.0 g. n-butyl bromide, and 4.2 g. of anhydrous potassium carbonate in 100 ml. of acetone are refluxed overnight with stirring. The mixture is evaporated, diluted with water and extracted with ether to afford 1-acetamido-4-n-butoxy-2-nitrobenzene. This latter compound is treated in accordance with the second paragraph of Example XXXI to afford 1-amino-4-n-butoxy-2-nitrobenzene. This latter compound is treated in accordance with the first paragraph of Example VI to afford 4-n-butoxy-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzene. This latter compound is treated in accordance with the iron reduction technique set forth in the third paragraph of Example XIX to afford 2-amino-4-n-butoxy-1-(3-methoxycarbonyl-2-thioureido)benzene. This latter compound is treated in accordance with the first paragraph of Example XVII to afford 4-n-butoxy-1-(3-methoxycarbonyl-2-thioureido)-2-succinamidobenzene.

Workup

  1. customThe mixture is evaporated
  2. additiondiluted with water
  3. extractionextracted with ether

Sources & evidence

ORD record
ord-eb6fbe724eb44ed68bb08fd73fc2eb89
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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