1,1'-Carbonyldiimidazole → 4-Nitro-N-(2-hydroxy-2-methyl-propyl)-3,5-dimethyl-benzamide

HRID 471441Notes

Reaction equation

HRID 471441 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:14])[C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:27][CH2:28][C:29]([CH3:32])([OH:31])[CH3:30]>O1CCCC1>[N+:11]([C:10]1[C:9]([CH3:14])=[CH:8][C:4]([C:5]([NH:27][CH2:28][C:29]([OH:31])([CH3:32])[CH3:30])=[O:7])=[CH:3][C:2]=1[CH3:1])([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 951022-Propanol, 1-amino-2-methyl-HCID 2494133,5-Dimethyl-4-nitrobenzoic acid

Product 1

HCID 867038834-Nitro-N-(2-hydroxy-2-methyl-propyl)-3,5-dimethyl-benzamideYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,5-Dimethyl-4-nitrobenzoic acid (1 g, 5.12 mmol) is suspended in dry tetrahydrofuran (10 mL) and 1,1′-carbonyldiimidazole (0.91 g, 5.64 mmol) is added. The mixture is stirred for 3 hours then 1-amino-2-methyl-propan-2-ol (patent WO2010/84767, 1 g, 11.22 mmol) is added and the mixture stirred for 30 minutes. The solvent is removed, the residue suspended in EtOAc and washed with 0.2 M aqueous HCl solution, saturated sodium bicarbonate solution and brine, dried and the solvent removed under vacuum to give the title compound (Yield 1.2 g).

Workup

  1. stirringthe mixture stirred for 30 minutes
  2. customThe solvent is removed
  3. washwashed with 0.2 M aqueous HCl solution, saturated sodium bicarbonate solution and brine
  4. customdried
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-b0e1d67c0bf64016b4a95aefbf446517
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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