Chloride → 2-nitro-N-isopropyl-5-phenoxybenzamide

HRID 2099965Notes

Reaction equation

HRID 2099965 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].[Cl-].[CH:21]([NH:24]C(C)C)([CH3:23])[CH3:22]>C(Cl)Cl.CN(C=O)C>[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][C:5]=1[C:6]([NH:24][CH:21]([CH3:23])[CH3:22])=[O:8])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 312ChlorideHCID 7912DiisopropylamineHCID 142334252-Nitro-5-phenoxybenzoic acid

Product 1

HCID 577968982-nitro-N-isopropyl-5-phenoxybenzamideYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 34A (1.0 g, 3.86 mmol) in CH2Cl2 (15 mL) was treated with one drop of DMF. Oxaly chloride (2.2 mL, 2M in CH2Cl2, 4.4 mmol) was added dropwise at room temperature. The reaction mixture was stirred for 1 hour, and then concentrated to dryness. The crude acid chloride was dissolved in CH2Cl2 and cooled to 0° C. Diisopropylamine (600 mg, 10 mmol) in CH2Cl2 (2 mL) was added slowly and the resulting mixture was stirred for one hour at room temperature. The reaction was concentrated and partitioned between EtOAc (20 mL) and 1M HCl (20 mL). The organic layer was washed with 1 M HCl (20 mL), saturated aqueous NaHCO3 (20 mL), and brine (20 mL). The organic layer was dried (Na2SO4), filtered, and concentrated to a brown solid. The crude amide was recrystallized from EtOAc/heptane to afford 34B (740 mg, 64%).

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe crude acid chloride was dissolved in CH2Cl2
  3. stirringthe resulting mixture was stirred for one hour at room temperature
  4. concentrationThe reaction was concentrated
  5. custompartitioned between EtOAc (20 mL) and 1M HCl (20 mL)
  6. washThe organic layer was washed with 1 M HCl (20 mL), saturated aqueous NaHCO3 (20 mL), and brine (20 mL)
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated to a brown solid
  10. customThe crude amide was recrystallized from EtOAc/heptane

Sources & evidence

ORD record
ord-6fc74c5f849a4f11a6c0a473d0678f37
Source dataset
uspto-grants-2009_08
Patent number
US07569725B2

Reaction notes

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