Dimethylformamide → Methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate

HRID 1874963Notes

Reaction equation

HRID 1874963 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[Cl:7][C:8]1[CH:9]=C(C(O)=O)[NH:11][C:12]=1[C:13]([O:15][CH3:16])=[O:14].CN(C=O)C>C(Cl)Cl>[Cl:7][C:8]1[CH:9]=[C:1]([C:2]([Cl:4])=[O:3])[NH:11][C:12]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 684860074-Chloro-5-[(methyloxy)carbonyl]-1H-pyrrole-2-carboxylic acid

Product 1

HCID 86644903Methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.430 mL, 4.91 mmol) was added to a solution of 4-chloro-5-[(methyloxy)carbonyl]-1H-pyrrole-2-carboxylic acid (0.500 g, 2.45 mmol) in DCM (50 mL). DMF (9.51 μl, 0.123 mmol) was added to the reaction mixture and the resulting suspension was stirred overnight. The solvent was evaporated to afford the title compound as a crude product (0.804 g) which was used with no further purification. 1H NMR (400 MHz, CDCl3) δ ppm 11.02 (s, 1H), 7.11 (d, 1H), 3.97 (s, 3H).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c85082ad817640dca3439079bacee753
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…