Triethylamine → 2-Fluoro-5-iodo-N-methylbenzamide

HRID 606818Notes

Reaction equation

HRID 606818 reaction equation
Cl.CN.[CH2:4]([N:6](CC)CC)C.[F:11][C:12]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:13]=1[C:14](Cl)=[O:15]>ClCCl>[F:11][C:12]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:13]=1[C:14]([NH:6][CH3:4])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27782042-Fluoro-5-iodobenzoyl chlorideHCID 6364545Methylamine hydrochloride

Product 1

HCID 670476742-Fluoro-5-iodo-N-methylbenzamideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add methylamine hydrochloride (0.57 g, 8.4 mmol) and triethylamine (2.17 mL, 15.5 mmol) to a solution of 2-fluoro-5-iodobenzoyl chloride (2.0 g, 7.0 mmol) in dichloromethane (100 mL) at 0° C. Warm to room temperature and stir 20 h. Concentrate and purify by silica gel chromatography, eluting with a gradient of 75:25 to 60:40 hexanes:ethyl acetate, to give the title compound as a white solid (1.7 g, 87%).

Workup

  1. concentrationConcentrate
  2. custompurify by silica gel chromatography
  3. washeluting with a gradient of 75:25 to 60:40 hexanes

Sources & evidence

ORD record
ord-8e951beab54c4d9cb3135a70879e971c
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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