Hydrochloric Acid → 4-Nitro-N,N-dipropylbenzamide

HRID 2295483Notes

Reaction equation

HRID 2295483 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:13]([NH:16][CH2:17][CH2:18][CH3:19])[CH2:14][CH3:15].Cl>CCOCC>[CH2:13]([N:16]([CH2:17][CH2:18][CH3:19])[C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 8902Dipropylamine

Product 1

HCID 3479374-Nitro-N,N-dipropylbenzamideYield 88.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

An amount of 37.1 gm (0.2 mol) of p-nitrobenzoyl chloride in 300 ml of ether were added dropwise, with agitation and at room temperature, into a solution of 50.6 gm (0.5 mol) of dipropylamine in 400 of ether. Then, the mixture was agitated for one hour at room temperature and one hour at boiling temperature, the reaction mixture was treated with dilute hydrochloric acid, and the ether phase washed with water and evaporated. An amount of 44.3 gm of p-nitrobenzoic acid dipropylamide in the form of a light-yellow, oily residue was obtained.

Workup

  1. washthe ether phase washed with water
  2. customevaporated

Sources & evidence

ORD record
ord-b6f7e71da5d44b99b681caf86c3b8661
Source dataset
uspto-grants-1984_01
Patent number
US04425327

Reaction notes

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