Ammonium Hydroxide → HCID 68721796, compound

HRID 1875266Notes

Reaction equation

HRID 1875266 reaction equation
[OH-].[NH4+:2].[Cl:3][C:4]1[N:5]=[C:6]([S:26](Cl)(=[O:28])=[O:27])[N:7]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:8]=1[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]>CC(C)=O.C1COCC1>[Cl:3][C:4]1[N:5]=[C:6]([S:26]([NH2:2])(=[O:28])=[O:27])[N:7]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:8]=1[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 86761669HCID 86761669, compound

Product 1

HCID 68721796HCID 68721796, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ammonium hydroxide (5.0 mL, 128 mmol) was added to a 0° C. solution of 4-chloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-2-sulfonyl chloride (1.33 g, 2.8 mmol) in acetone (4.5 mL) and THF (2.5 mL). The reaction mixture was stirred at RT for 30 min and evaporated. The residue was taken up in EtOAc and washed with brine. The organic phase was dried (Na2SO4), filtered, evaporated, and purified by silica gel chromatography (0-25% EtOA/hexanes) to give the title compound (0.95 g, 74%) as a light yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.71 (s, 2H), 5.37 (br. s., 2H), 4.75 (s, 2H), 3.59-3.70 (m, 2H), 0.92-0.97 (m, 2H), 0.91 (s, 9H), 0.11 (s, 6H), 0.02 (s, 9H).

Workup

  1. customevaporated
  2. washwashed with brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by silica gel chromatography (0-25% EtOA/hexanes)

Sources & evidence

ORD record
ord-ab9e47ea452841cd88d9ff18ec2ff683
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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