3-Chloro-2-nitrobenzoic acid → N-(diethylphosphonomethyl)-2-nitro-3-chlorobenzamide

HRID 895996

Reaction equation

HRID 895996 reaction equation
[Cl:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[PH:14]1(=[O:23])[O:21][CH2:20][CH2:19]C(N)[CH2:17][CH2:16][O:15]1.[CH:24]([N:27](C(C)C)CC)(C)C>ClCCl>[CH2:20]([O:21][P:14]([CH2:24][NH:27][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[C:3]=1[N+:11]([O-:13])=[O:12])([O:15][CH2:16][CH3:17])=[O:23])[CH3:19]

Participants

5

Reactant 3

HCID 209023-Chloro-2-nitrobenzoic acidHCID 81531DiisopropylethylamineHCID 178507970HCID 178507970, compound

Product 1

HCID 57457785N-(diethylphosphonomethyl)-2-nitro-3-chlorobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-2-nitrobenzoic acid (1 mmol) and aminomethylenediethyl phosphonate (1.1 mmol) in dichloromethane (5 mL)was added diisopropylethylamine (5 mmol) followed by pyBOP (1.5 mmol). The reaction was stirred at room temperature for 3 h and concentrated. The mixture was purified by chromatography to yield N-(diethylphosphonomethyl)-2-nitro-3-chlorobenzamide as a solid.

Workup

  1. concentrationconcentrated
  2. customThe mixture was purified by chromatography

Sources & evidence

ORD record
ord-5b4ce0306a5243a7af705ac0b7c6c3d6
Source dataset
uspto-grants-2005_07
Patent number
US06919322B2

Linked notes

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