Dimethylformamide → Ethyl 3-(chlorocarbonyl)-5-nitrobenzoate

HRID 241691Notes

Reaction equation

HRID 241691 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:7]([C:8](O)=[O:9])[CH:6]=1)[CH3:2].C(Cl)(=O)C([Cl:21])=O.CN(C=O)C>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:7]([C:8]([Cl:21])=[O:9])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 898721,3-Benzenedicarboxylic acid, 5-nitro-, 1-ethyl ester

Product 1

HCID 3023043Ethyl 3-(chlorocarbonyl)-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-nitroisophtalic acid monoethyl ester (80 g) in DCM (700 ml) at 25° C. was added 2M oxalyl chloride solution in DCM (63 ml), and DMF (5 ml). The reaction was stirred for 2 h and then concentrated in vacuum. The residue was triturated with toluene and again concentrated in vacuum leaving the title compound (60 g). Rt=1.40 min for derivatised methylester (method D).

Workup

  1. concentrationconcentrated in vacuum
  2. customThe residue was triturated with toluene
  3. concentrationagain concentrated in vacuum

Sources & evidence

ORD record
ord-89ff3df1b9c440828a0b7e0e11fd4b19
Source dataset
uspto-grants-2014_02
Patent number
US08653075B2

Reaction notes

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