Silicon tetrachloride → HCID 70496380, compound

HRID 2408049Notes

Reaction equation

HRID 2408049 reaction equation
Cl[Si](Cl)(Cl)Cl.[N-:6]=[N+:7]=[N-:8].[Na+].[CH2:10]([O:12][C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31](=O)[NH:32][CH3:33])[CH:26]=1)[CH2:19][C:18]2([CH3:36])[CH3:35])=[O:14])[CH3:11]>C(#N)C>[CH2:10]([O:12][C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]3[N:32]([CH3:33])[N:8]=[N:7][N:6]=3)[CH:26]=1)[CH2:19][C:18]2([CH3:35])[CH3:36])=[O:14])[CH3:11]

Participants

5

Reactant 3

HCID 24816Silicon tetrachlorideHCID 33557Sodium AzideHCID 70495722HCID 70495722, compound

Product 1

HCID 70496380HCID 70496380, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of tetrachlorosilane (5.3 mL, 46.3 mmol), sodium azide (5.6 g, 87 mmol) in dry acetonitrile (20 mL) was added 4,4-dimethyl-2-(3-methylcarbamoyl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (1.23 g, 3.3 mmol) at room temperature. Then the mixture solution was stirred at room temperature for over night. LC/MS showed that reaction finished completely. The reaction mixture was poured into ice-cold saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate (150 mL×2), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (30% ethyl acetate/hexanes) afforded 4,4-dimethyl-2-[3-(1-methyl-1H-tetrazol-5-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (851.6 mg, 66%) as a white solid: MS (ESI) M+1=392.1.

Workup

  1. customLC/MS showed that reaction
  2. additionThe reaction mixture was poured into ice-cold saturated aqueous sodium bicarbonate solution
  3. extractionextracted with ethyl acetate (150 mL×2)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-dbb2f4bf2cf54eb09e952452587c6c39
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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