Dimethylformamide → HCID 86761668, compound

HRID 1875254Notes

Reaction equation

HRID 1875254 reaction equation
[Li]CCCC.[Cl:6][C:7]1[N:8]=[C:9]([S:21]([N:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1Cl.CN([CH:30]=[O:31])C>C1COCC1>[Cl:6][C:7]1[N:8]=[C:9]([S:21]([N:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1[CH:30]=[O:31]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70937249HCID 70937249, compoundHCID 178418339Butyllithium

Product 1

HCID 86761668HCID 86761668, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

nBuLi (0.21 ml of a 2.4M solution in hex, 0.51 mmol) was added dropwise to a −78° C. solution of 4,5-dichloro-N,N-dimethyl-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-2-sulfonamide (0.18 g, 0.47 mmol) in THF (3 ml). The reaction mixture was stirred for 30 mins and DMF (0.4 ml, 5.17 mmol) was added. After 10 mins, the cooling bath was removed and the reaction mixture was warmed to RT. Sat'd NaHCO3 was added and the solution was extracted with EtOAc. The organic layer was dried (Na2SO4), filtered, evaporated, and purified by silica gel chromatography (0-20% EtOAc/hexanes) to provide the title compound (0.085 g, 49%) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.93 (s, 1H), 5.94 (s, 2H), 3.63-3.70 (m, 2H), 3.09 (s, 6H), 0.89-0.98 (m, 2H), −0.02 (s, 9H).

Workup

  1. waitAfter 10 mins
  2. customthe cooling bath was removed
  3. additionSat'd NaHCO3 was added
  4. extractionthe solution was extracted with EtOAc
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. custompurified by silica gel chromatography (0-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f683d8c8fd754c399358ce418b7f756c
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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