Ammonium Chloride → 2-(tert-Butyl-dimethyl-silyl)-5-(4-methyl-3-nitro-benzyl)-imidazole-1-sulfonic acid dimethylamide

HRID 1106744Notes

Reaction equation

HRID 1106744 reaction equation
[CH3:1][N:2]([CH3:18])[S:3]([N:6]1[CH2:10][CH2:9][N:8]=[C:7]1[Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])(=[O:5])=[O:4].C([Li])CCC.Br[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:1][N:2]([CH3:18])[S:3]([N:6]1[C:10]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=2)=[CH:9][N:8]=[C:7]1[Si:11]([C:14]([CH3:15])([CH3:17])[CH3:16])([CH3:13])[CH3:12])(=[O:4])=[O:5]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 126236744-(Bromomethyl)-1-methyl-2-nitrobenzeneHCID 536506332-(tert-Butyl-dimethyl-silyl)-4,5-dihydro-imidazole-1-sulfonic acid dimethylamideHCID 178418339Butyllithium

Product 1

HCID 539951302-(tert-Butyl-dimethyl-silyl)-5-(4-methyl-3-nitro-benzyl)-imidazole-1-sulfonic acid dimethylamideYield 31.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-(tert-Butyl-dimethyl-silyl)-4,5-dihydro-imidazole-1-sulfonic acid dimethylamide (5.03 g) (prepared as described by Ngochindo, J. Chem. Soc. Perkin Trans. (1990) 1:1645) was dissolved in 100 ml of dry tetrahydrofuran and cooled in a dry ice-acetone bath to -78° C.; 11.9 ml of 1.6M n-butyllithium in hexane was added to this mixture. After 1 hr at -78° C., the reaction mixture was treated dropwise with 5.0 g of 4-bromomethyl-1-methyl-2-nitro-benzene dissolved in 25 ml of dry tetrahydrofuran (THF). The mixture was stirred at -78° C. for 1 hr and then allowed to come to room temperature overnight. The mixture was treated with saturated ammonium chloride, extracted with ethyl acetate washed the combined extracts with saturated sodium chloride, dried, and evaporated to dryness. The residue was purified by flash chromatography on silica gel and eluted with ethyl acetate:hexane (1:4 ) to give 2.39 g of 2-(tert-butyl-dimethyl-silyl)-5-(4-methyl-3-nitro-benzyl)-imidazole-1-sulfonic acid dimethylamide as a yellow oil. ##STR126##

Workup

  1. waitto come to room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washwashed the combined extracts with saturated sodium chloride
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluted with ethyl acetate:hexane (1:4 )

Sources & evidence

ORD record
ord-433e74c1294a4b09ac12988df54b1555
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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