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

HRID 2222111

Reaction equation

HRID 2222111 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-b600187e708946b089bdc25769d32996
Source dataset
uspto-grants-2008_05
Patent number
US07371739B2

Linked notes

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