Water → Methyl 4-[(4,5-dichloro-2-fluoro-benzoyl)amino]benzoate

HRID 515097Notes

Reaction equation

HRID 515097 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([F:12])[CH:3]=1.[NH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1.N1C=CC=CC=1.O>ClCCl>[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=2)=[O:7])=[C:4]([F:12])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 12082Methyl 4-aminobenzoateHCID 196123744,5-Dichloro-2-fluorobenzoylchloride

Product 1

HCID 90314713Methyl 4-[(4,5-dichloro-2-fluoro-benzoyl)amino]benzoateYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4,5-dichloro-2-fluoro-benzoyl chloride (794.5 mg, 3.49 mmol) in dichloromethane (7.3 mL) was added drop-wise to a mixture of methyl 4-aminobenzoate (528.0 mg, 3.49 mmol), pyridine (847.6 μL, 10.48 mmol) and dichloromethane (11.0 mL) at 0° C. The reaction was stirred and allowed to warm up to room temperature over 1.5 hours. To the reaction, water (10 mL) was added. The solid was isolated by filtration, washed with water (2×10 mL) and hexane (2×10 mL) to yield methyl 4-[(4,5-dichloro-2-fluoro-benzoyl)amino]benzoate (955 mg, 80%) as a light pink solid. ESI-MS m/z calc. 341.00, found 342.2 (M+1)+; Retention time: 1.75 minutes (3 minutes run). 1H NMR (400 MHz, DMSO-d6) δ 10.90 (s, 1H), 8.03 (d, J=6.7 Hz, 1H), 8.02-7.95 (m, 2H), 7.93 (d, J=9.4 Hz, 1H), 7.88-7.76 (m, 2H), 3.84 (s, 3H) ppm.

Workup

  1. additionwas added
  2. customThe solid was isolated by filtration
  3. washwashed with water (2×10 mL) and hexane (2×10 mL)

Sources & evidence

ORD record
ord-4c044e9a89234107b307407ede15e97f
Source dataset
uspto-grants-2015_08
Patent number
US09108903B2

Reaction notes

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