Triethylamine → N-(3-chloropropyl)-4-nitrobenzamide

HRID 413976

Reaction equation

HRID 413976 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][NH2:5].C(N(CC)CC)C.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14]>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:20](=[O:21])[C:19]1[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 846293-Chloropropylamine

Product 1

HCID 3421653N-(3-chloropropyl)-4-nitrobenzamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6.43 g (49 mmol) 3chloropropylamine and 13.6 ml (98 mmol) triethylamine in 220 ml methylene chloride was cooled by an ice bath and 9 g (48.5 mmol) 4-nitrobenzoyl chloride were added fractionwise. After one hour stirring at room temperature the organic phase was washed twice with water, dried over MgSO4 and concentrated in vacuo to afford 10.68 g (91%) of beige crystals. 1H NMR was consistent with the desired structure.

Workup

  1. washwas washed twice with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05c21b4c0a3e4e1bb8ccb86f776fa136
Source dataset
uspto-grants-2003_05
Patent number
US06570037B2

Linked notes

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