Silicon tetrachloride → HCID 178424084, compound

HRID 2357644Notes

Reaction equation

HRID 2357644 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=O)=[CH:4][C:3]=1[B:11]1[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]1.[N-:20]=[N+:21]=[N-:22].[Na+].O1CCOCC1.[Si](Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[NH:22][N:21]=[N:20][N:8]=2)=[CH:4][C:3]=1[B:11]1[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]1

Participants

6

Reactant 4

HCID 24816Silicon tetrachlorideHCID 312751,4-DioxaneHCID 33557Sodium AzideHCID 595448534-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Product 1

HCID 178424084HCID 178424084, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
85 °C

Procedure

4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.27 g, 1.0 mmol) and sodium azide (0.20 g, 3.1 mmol) were added to dioxane (5.2 mL, 1.0 mmol) before silicon tetrachloride (0.12 mL, 1.0 mmol) was added. The reaction mixture was heated to 85° C. for 7 h when two spots were observed by tlc. The reaction mixture was stirred at 60° C. overnight. The reaction mixture was diluted with 50 mL chloroform, partitioned with brine (saturated, aqueous), washed 2 times with 50 mL of chloroform, separated, dried over sodium sulfate, and concentrated in vacuo to give the title compound. MS (ES+): 287 (M+H)+.

Workup

  1. additionwas added
  2. custompartitioned with brine (saturated, aqueous)
  3. washwashed 2 times with 50 mL of chloroform
  4. customseparated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a968ad0804f04a6c94e76e07db64e0e4
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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