Cyanuric chloride → HCID 15325922, compound

HRID 522522Notes

Reaction equation

HRID 522522 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5]([Cl:6])=[N:4][C:2]=1Cl.[C:10]([Mg]Cl)([CH3:13])([CH3:12])[CH3:11].[NH4+].[Cl-]>C1COCC1.[Cu]I>[C:10]([C:2]1[N:4]=[C:5]([Cl:6])[N:7]=[C:8]([Cl:9])[N:1]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 7954Cyanuric chlorideHCID 25517Ammonium ChlorideHCID 178418310HCID 178418310, compound

Product 1

HCID 15325922HCID 15325922, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

Dissolved cyanuric chloride (4.2 g, 22.9 mmol) and CuI (0.22 g, 1.1 mmol) in anhydrous THF (12 mL) and cooled to −10° C. under N2. Added tert-butylmagnesium chloride (1.0M in THF, 25.4 mL) slowly over 20 min. Added saturated NH4Cl (5 mL) and warmed reaction to room temperature. Extracted mixture with CH2Cl2 (4×75 mL). Washed organic layer with water (35 mL) and saturated NaCl (35 mL) then dried (Na2SO4) and concentrated. Purified the product by filtration through a pad of silica gel eluting with CH2Cl2 to give the title compound (1.5 g) as a yellow oil.

Workup

  1. customreaction to room temperature
  2. extractionExtracted mixture with CH2Cl2 (4×75 mL)
  3. dry with materialWashed organic layer with water (35 mL) and saturated NaCl (35 mL) then dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurified the product
  6. filtrationby filtration through a pad of silica gel eluting with CH2Cl2

Sources & evidence

ORD record
ord-d18a01a6ea5a4060b9854e5a5c096935
Source dataset
uspto-grants-2016_05
Patent number
US09334246B2

Reaction notes

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