Potassium Iodide → 4-iodo-N,3,5-trimethylbenzamide

HRID 471448Notes

Reaction equation

HRID 471448 reaction equation
N[C:2]1[C:11]([CH3:12])=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:13].N([O-])=O.[Na+].[I-:18].[K+]>Cl.O.ClCCl>[I:18][C:2]1[C:11]([CH3:12])=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:13]

Participants

7

Reactant 3

HCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 668742744-amino-N,3,5-trimethylbenzamide

Product 1

HCID 866971824-iodo-N,3,5-trimethylbenzamide

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Amino-3,5,N-trimethyl-benzamide (850 mg, 4.77 mmol) is suspended in hydrochloric acid (37%, 2 mL), stirred until completely dissolved then cooled to 0° C. Sodium nitrite (494 mg, 7.15 mmol) in water (0.5 mL) is added and the mixture stirred for 1 hour at 0° C. Potassium iodide (2.38 g, 14.31 mmol) in 1.5 mL water is added and the mixture stirred for 15 minutes. The mixture is diluted with dichloromethane then washed with 10% aqueous sodium thosulfate solution, dried and the solvent removed under vacuum. The residue is purified by flash chromatography (0-50% ethyl acetate in cyclohexane) to give the title compound. (Yield 850 mg).

Workup

  1. dissolutionuntil completely dissolved
  2. stirringthe mixture stirred for 1 hour at 0° C
  3. stirringthe mixture stirred for 15 minutes
  4. washthen washed with 10% aqueous sodium thosulfate solution
  5. customdried
  6. customthe solvent removed under vacuum
  7. customThe residue is purified by flash chromatography (0-50% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-be1b6d7af2234ded89d6acf5535eb323
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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