Water → N-Isopropyl-4-nitrobenzamide

HRID 2226083Notes

Reaction equation

HRID 2226083 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[OH-].[Na+].[N+:7]([C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1)([O-:9])=[O:8].O>CC(C)=O>[CH:1]([NH:4][C:14](=[O:15])[C:13]1[CH:12]=[CH:11][C:10]([N+:7]([O-:9])=[O:8])=[CH:18][CH:17]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6363IsopropylamineHCID 85024-Nitrobenzoyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 347926N-Isopropyl-4-nitrobenzamideYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
0 °C

Procedure

32.5 g of isopropylamine dissolved in 250 ml of acetone are added with 71 g of a 30% sodium hydroxide aqueous solution. This mixture, cooled to 0° C., is slowly added with 92.7 g of p-nitrobenzoyl chloride dissolved in 300 ml of acetone, coo ling with an ice bath to keep temperature from 0° to 5° C. Subsequently stirring is continued for 1 more hour allowing temperature to raise to 20°-30° C. Then the reaction mixture is poured into cold water. The formed precipitate is filtered, washed with water, dried and crystallized from isopropanol. 77 g of N-isopropyl-p-nitrobenzamide are obtained as a whitish solid substance with m.p. 152°-154° C.

Workup

  1. customcoo ling with an ice bath to keep
  2. customfrom 0° to 5° C
  3. temperatureto raise to 20°-30° C
  4. filtrationThe formed precipitate is filtered
  5. washwashed with water
  6. customdried
  7. customcrystallized from isopropanol

Sources & evidence

ORD record
ord-dea016e19abc42ee812b3ce97e7cf901
Source dataset
uspto-grants-1994_09
Patent number
US05346691

Reaction notes

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