Dimethylamine → HCID 70937249, compound

HRID 1875253Notes

Reaction equation

HRID 1875253 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([S:16](Cl)(=[O:18])=[O:17])[N:5]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[Cl:7].[CH3:20][NH:21][CH3:22]>CC(C)=O.C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([S:16]([N:21]([CH3:22])[CH3:20])(=[O:18])=[O:17])[N:5]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[Cl:7]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 86761667HCID 86761667, compound

Product 1

HCID 70937249HCID 70937249, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4,5-dichloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-2-sulfonyl chloride (0.826 mmol) in acetone (2.5 mL) and THF (1.5 mL) was added to dimethylamine (2.0 mL of a 2M solution in THF, 4.0 mmol). The reaction mixture was stirred at RT for 1 h and then evaporated to dryness. The residue was taken up in EtOAc and washed with brine. The organic layer was dried (Na2SO4), filtered, evaporated and purified by silica gel chromatography (0-30% EtOAc/hexanes) to provide the title compound (0.18 g, 57%) as a light yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.62 (s, 2H), 3.61-3.75 (m, 2H), 3.06 (s, 6H), 0.84-1.00 (m, 3H), 0.00 (s, 9H).

Workup

  1. customevaporated to dryness
  2. washwashed with brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by silica gel chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-591906ea80d54603b8677c7cd3a9a502
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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