Potassium Iodide → HCID 21916139, compound

HRID 1349409Notes

Reaction equation

HRID 1349409 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[Cl:14])=[O:4].[I-].[K+].[N-:17]=[N+:18]=[N-:19].[Na+].CN(C)C=O>O>[N:17]([CH2:2][C:3]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[Cl:14])=[O:4])=[N+:18]=[N-:19]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 33557Sodium AzideHCID 2110931HCID 2110931, compound

Product 1

HCID 21916139HCID 21916139, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-Chloro-N-(2-chloro-4,6-dimethyl-phenyl)-acetamide (0.100 g, 0.00043 mol), potassium iodide (0.0072 g, 0.00043 mol), sodium azide (0.056 g, 0.00086 mol), and anhydrous dimethylformamide (7 mL) was heated in a 50° C. oil bath for 4 h. Upon cooling to room temperature, the reaction mixture was cooled to 0° C., water (10 mL) was added, and the solid product was collected by suction filtration, washed several times with water, and placed in a vacuum oven set at low heat for 4 h. The dried product amounted to 0.0934 g (0.391 mmol, 91%). 1H NMR (CDCl3, 300 MHz) δ 7.70 (br s 1H), 7.12 (s, 1H), 6.98 (s, 1H), 4.2 (s, 2H), 2.3 (s, 3H), 2.23 (s, 3H). LC/MS: tR=1.23 min., (MH+)=239.06.

Workup

  1. temperatureUpon cooling to room temperature
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. filtrationthe solid product was collected by suction filtration
  4. washwashed several times with water
  5. temperatureat low heat for 4 h

Sources & evidence

ORD record
ord-b9dd04a35c1d470ab061f4cb1a2d549c
Source dataset
uspto-grants-2007_05
Patent number
US07211669B2

Reaction notes

Loading…