Triethylamine → N-Decyl-4-nitrobenzamide

HRID 1757864Notes

Reaction equation

HRID 1757864 reaction equation
[CH2:1]([NH2:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(N(CC)CC)C.[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20]>C(Cl)Cl>[CH2:1]([NH:11][C:26]([C:25]1[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:30][CH:29]=1)=[O:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 8916Decylamine

Product 1

HCID 3414942N-Decyl-4-nitrobenzamideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5.4 ml (0.027 mol) of decylamine and 5.6 ml (0.04 mol) of triethylamine in 20 ml of methylene chloride cooled in an ice bath was added dropwise a solution of 5.0 g (0.027 mol) of 4-nitrobenzoyl chloride in 40 ml of methylene chloride. The reaction mixture was stirred in the ice bath for 30 minutes, at room temperature for 15 minutes and kept at 0° for 18 hours. After dilution with methylene chloride, the mixture was washed with 0.5N NaOH and the extract was dried and concentrated to a solid. Recrystallization from methylene chloride-hexane gave 8.1 g (98% yield, mp 89°-91°) of 4-[(decylamino)carbonyl]nitrobenzene. The nmr was consistent with the structure.

Workup

  1. washAfter dilution with methylene chloride, the mixture was washed with 0.5N NaOH
  2. customthe extract was dried
  3. concentrationconcentrated to a solid
  4. customRecrystallization from methylene chloride-hexane

Sources & evidence

ORD record
ord-9fa2084cfd424076bc24631fb1642cec
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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