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

HRID 1601338

Reaction equation

HRID 1601338 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-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6.43 g (49 mmol) 3-chloropropylamine 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
  4. customto afford 10.68 g (91%)

Sources & evidence

ORD record
ord-f96156a5394c4311839ffe582a66b357
Source dataset
uspto-grants-1999_11
Patent number
US05977179

Linked notes

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