Nitrogen → HCID 131730004, compound

HRID 1044747Notes

Reaction equation

HRID 1044747 reaction equation
N#N.[Li]CCCC.Br[C:9]1[S:10][C:11]([C:14]([CH3:22])([CH3:21])[O:15][SiH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:12][N:13]=1.CN(C)[C:25](=[O:27])[CH3:26].[NH4+].[Cl-]>CCOCC>[C:17]([SiH2:16][O:15][C:14]([CH3:22])([CH3:21])[C:11]1[S:10][C:9]([C:25](=[O:27])[CH3:26])=[N:13][CH:12]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 5

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 131730005HCID 131730005, compoundHCID 178418339Butyllithium

Product 1

HCID 131730004HCID 131730004, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of n-BuLi (4.3 mL of a 2.5 M solution in hexanes, 10.75 mmol) in dry Et2O (15 mL) was added a solution of 2-bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-thiazole (3.03 g, 9.83 mmol) in dry Et2O (10 mL) at −78° C. The reaction mixture was then stirred for 30 min at −78° C. before N,N-dimethylacetamide (1.9 mL, 20.43 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 1 h. Sat. aq. NH4Cl (20 mL) was added, the layers separated and the aq. layer extracted with Et2O (2×30 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to give the title compound as an orange oil. TLC:rf (2:1 hept-EA)=0.60. LC-MS-conditions 02: tR=1.14 min; [M+H]+=272.32.

Workup

  1. additionwas added dropwise
  2. customthe layers separated
  3. extractionthe aq. layer extracted with Et2O (2×30 mL)
  4. dry with materialextracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-59782cd9c2704064b0e5190bbb5c19ba
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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