Ammonia → 2-Methyl-2-(4-nitrophenoxy)propanamide

HRID 1725703Notes

Reaction equation

HRID 1725703 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][C:9]([CH3:14])([CH3:13])[C:10](O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].ClC(OCC(C)C)=O.C([N:27](CC)CC)C.N>ClCCl.CO>[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][C:9]([CH3:14])([CH3:13])[C:10]([NH2:27])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 1769302-Methyl-2-(4-nitrophenoxy)propanoic acid

Product 1

HCID 123215222-Methyl-2-(4-nitrophenoxy)propanamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2-(4-Nitrophenoxy)isobutyric acid (5 g), isobutyl chloroformate (4.36 mL) and triethylamine (8 mL) were stirred in dichloromethane (20 mL) at rt for 1 h. Then 2.0 M ammonia in methanol (20 mL) was added to the solution. It was stirred at rt for 2 h and evaporated. The mixture was purified by recrystallization from EtOAc and hexanes to give 2-(4-nitrophenoxy)-2-methylpropanamide.

Workup

  1. customevaporated
  2. customThe mixture was purified by recrystallization from EtOAc and hexanes

Sources & evidence

ORD record
ord-21888b64d218492ab93d457d0f2ca4ca
Source dataset
uspto-grants-2009_02
Patent number
US07491732B2

Reaction notes

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