Nitrogen → HCID 131729999, compound

HRID 1044737Notes

Reaction equation

HRID 1044737 reaction equation
N#N.Br[C:4]1[N:5]=[C:6]([C:9]([CH3:17])([CH3:16])[O:10][SiH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[S:7][CH:8]=1.[Li]CCCC.CN(C)[C:25](=[O:27])[CH3:26].[NH4+].[Cl-]>CCOCC>[C:12]([SiH2:11][O:10][C:9]([CH3:17])([CH3:16])[C:6]1[S:7][CH:8]=[C:4]([C:25](=[O:27])[CH3:26])[N:5]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 5

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 131730000HCID 131730000, compoundHCID 178418339Butyllithium

Product 1

HCID 131729999HCID 131729999, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 4-bromo-2-(tert-butyl-dimethyl-silanyloxymethyl)-thiazole (1.94 g, 6.29 mmol) in dry Et2O (50 mL) was added n-BuLi (2.76 mL of a 2.5 M solution in hexanes, 6.92 mmol) at −78° C. The reaction mixture was then stirred for 30 min at −78° C. before N,N-dimethylacetamide (1.17 mL, 12.58 mmol) was added dropwise. The reaction mixture was allowed to warm up to rt over a period of 1 h and stirred at this temperature for 20 min. Sat. aq. NH4Cl (20 mL) was added, the layers separated and the aq. layer extracted with Et2O (3×30 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1->5:1 hept-EA) gave the title compound as a yellow solid. TLC:rf (1:1 hept-EA)=0.51. LC-MS-conditions 02: tR=1.11 min; [M+H]+=272.39.

Workup

  1. additionwas added dropwise
  2. customthe layers separated
  3. extractionthe aq. layer extracted with Et2O (3×30 mL)
  4. dry with materialextracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customPurification of the residue by FC (20:1->5:1 hept-EA)

Sources & evidence

ORD record
ord-38e95ec0804e46969a669c9cb2c9b54b
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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