Silicon tetrachloride → HCID 67441580, compound

HRID 1801210Notes

Reaction equation

HRID 1801210 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]([NH:31][C:32](=O)[CH2:33][CH3:34])[CH:26]=1)[C:19]([CH3:37])([CH3:36])[CH2:18]2)=[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]([N:31]3[C:32]([CH2:33][CH3:34])=[N:8][N:7]=[N:6]3)[CH:26]=1)[C:19]([CH3:37])([CH3:36])[CH2:18]2)=[O:14])[CH3:11]

Participants

5

Reactant 3

HCID 24816Silicon tetrachlorideHCID 33557Sodium AzideHCID 67443046HCID 67443046, compound

Product 1

HCID 67441580HCID 67441580, 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 3,3-dimethyl-2-(3-propionylamino-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (2.2 g, 5.8 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 (2×200 mL), 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 2-[3-(5-ethyl-tetrazol-1-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (1.5 g, 66%) as a white solid: LC/MS m/e calcd for C23H27N5O2 (M+H)+: 406.50, observed: 406.2.

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 (2×200 mL)
  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-0bd0e2d482684c78a6582f38e7f97393
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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