Ammonia → 2-Fluoro-5-iodobenzamide

HRID 606822Notes

Reaction equation

HRID 606822 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH3:12]>CO>[F:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([NH2:12])=[O:5]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 27782042-Fluoro-5-iodobenzoyl chloride

Product 1

HCID 670478112-Fluoro-5-iodobenzamideYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

Add slowly 2-fluoro-5-iodobenzoyl chloride (4.0 g, 14.1 mmol) to a 7 N solution of ammonia in methanol (20 mL, 141 mmol) cooled to 0° C. Stir at 0° C. for 45 min then warm to room temperature and stir 5 h. Add an additional amount of the 7 N solution of ammonia in methanol (20 mL) to the reaction mixture and stir for 15 h. Concentrate, dilute with ethyl acetate (300 mL) and wash twice with water (30 mL) and twice with an aqueous saturated solution of sodium chloride (30 mL). Dry (sodium sulfate), filter, and concentrate. Purify by silica gel chromatography, eluting with 60:40 to 40:60 hexanes:ethyl acetate, to give the title compound as a white solid (3.45 g, 92%).

Workup

  1. temperaturethen warm to room temperature
  2. stirringstir 5 h
  3. stirringstir for 15 h
  4. concentrationConcentrate
  5. additiondilute with ethyl acetate (300 mL)
  6. washwash twice with water (30 mL) and twice with an aqueous saturated solution of sodium chloride (30 mL)
  7. dry with materialDry (sodium sulfate)
  8. filtrationfilter
  9. concentrationconcentrate
  10. customPurify by silica gel chromatography
  11. washeluting with 60:40 to 40:60 hexanes

Sources & evidence

ORD record
ord-3ebac6051a7e46fd8a3f066fedf7a341
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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