Water → N-(2-hydroxy-1,1-dimethylethyl)-2-methyl-3-nitrobenzamide

HRID 621460Notes

Reaction equation

HRID 621460 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17].O>ClCCl.CC(O)C>[OH:17][CH2:16][C:15]([NH:14][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[CH3:1])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 118072-Amino-2-methyl-1-propanolHCID 121948722-Methyl-3-nitrobenzoyl chloride

Product 1

HCID 800749N-(2-hydroxy-1,1-dimethylethyl)-2-methyl-3-nitrobenzamide

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methyl-3-nitrobenzoyl chloride, 0.2 mol, (U.S. Pat. No. 4,065,477) in dichloromethane is added to 0.4 mol of 2-amino-2-methyl-1-propanol (Aldrich Chemical Company) with ice cooling. The mixture is allowed to stand overnight, water added and the solid filtered to give 20.8 g. The organic layer is washed with water, separated and evaporated to give 28.1 g. The two crops of material are combined and dissolved in 2-propanol. The 2-propanol solution is concentrated to give 40.2 g of N-(2-hydroxy-1,1-dimethylethyl)-2-methyl-3-nitrobenzamide; mp 144°-145° C.

Workup

  1. filtrationthe solid filtered
  2. customto give 20.8 g
  3. washThe organic layer is washed with water
  4. customseparated
  5. customevaporated
  6. customto give 28.1 g
  7. concentrationThe 2-propanol solution is concentrated

Sources & evidence

ORD record
ord-064c501dd0504678a270b783837eff70
Source dataset
uspto-grants-1989_04
Patent number
US04824843

Reaction notes

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