Dimethylformamide → Methyl 2-(2,6-dichloroanilino)benzoate

HRID 1461422Notes

Reaction equation

HRID 1461422 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].[CH3:19]N(C)C=O.C(Cl)(=O)C(Cl)=O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([O:14][CH3:19])=[O:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 151812N-(2,6-Dichlorophenyl)anthranilic acid

Product 1

HCID 13018920Methyl 2-(2,6-dichloroanilino)benzoateYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[(2,6-dichlorophenyl) amino]benzoic acid (25 g, 89 mmol) [J. S. Kaltenbronn et al, Arzneim-Forsch/Drug Res. 33(1),4a, 621-627 (1983)] and dimethylformamide (6.8 g, 93 mmol) in dry tetrahydrofuran (500 ml) is added oxalyl chloride (17 ml, 196 mmol) dropwise with stirring under an atmosphere of dry nitrogen at 0° C. The ice bath is removed and the reaction mixture is stirred without cooling for 15 minutes. The reaction mixture is poured into methanol (1500 ml). The solvent is evaporated and the residue is partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer is dried (MgSO4) and evaporated. Recrystallization of the residue from methanol provides pure 2-[(2,6-dichlorophenyl) amino]benzoic acid, methyl ester (21.9 g, 83%); mp 100°-103° C.

Workup

  1. customThe ice bath is removed
  2. stirringthe reaction mixture is stirred
  3. temperaturewithout cooling for 15 minutes
  4. additionThe reaction mixture is poured into methanol (1500 ml)
  5. customThe solvent is evaporated
  6. customthe residue is partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  7. dry with materialThe organic layer is dried (MgSO4)
  8. customevaporated
  9. customRecrystallization of the residue from methanol

Sources & evidence

ORD record
ord-bb271989a01a4b8baec953d0ebe3d254
Source dataset
uspto-grants-1991_12
Patent number
US05075330

Reaction notes

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