Dimethylamine → 2-Fluoro-5-iodo-N,N-dimethylbenzamide

HRID 606823Notes

Reaction equation

HRID 606823 reaction equation
[CH3:1][NH:2][CH3:3].O1CCCC1.[F:9][C:10]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][C:11]=1[C:12](Cl)=[O:13]>ClCCl>[F:9][C:10]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][C:11]=1[C:12]([N:2]([CH3:3])[CH3:1])=[O:13]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 27782042-Fluoro-5-iodobenzoyl chloride

Product 1

HCID 581814352-Fluoro-5-iodo-N,N-dimethylbenzamideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add a 2.0 M solution of dimethylamine in tetrahydrofuran (5 mL, 10.1 mmol) to a solution of 2-fluoro-5-iodobenzoylchloride (1.3 g, 4.6 mmol) in dichloromethane (20 mL) and stir at room temperature for 0.5 h. Sequentially wash the reaction mixture with a 1 N hydrochloric acid (50 mL), a 1 N sodium hydroxide (50 mL), and an aqueous saturated solution of sodium chloride (50 mL). Dry (sodium sulfate), filter, and concentrate to give the title compound as a white solid (1.3 g, 98%).

Workup

  1. washSequentially wash the reaction mixture with a 1 N hydrochloric acid (50 mL)
  2. dry with materialDry (sodium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-a50ddb75971c456cac34f4aac7ac11bd
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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