Ammonium Chloride → HCID 18779248, compound

HRID 1422308Notes

Reaction equation

HRID 1422308 reaction equation
[Si:1]([C:8]1[N:9]([S:13](=[O:18])(=[O:17])[N:14]([CH3:16])[CH3:15])[CH:10]=[CH:11][N:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]Br.[Cl-].[NH4+]>O1CCCC1.C(OCC)C>[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:10]1[N:9]([S:13](=[O:18])(=[O:17])[N:14]([CH3:15])[CH3:16])[C:8]([Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])=[N:12][CH:11]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 783101,8-DibromooctaneHCID 64202092-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamideHCID 178418339Butyllithium

Product 1

HCID 18779248HCID 18779248, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl) imidazole (Example 29 step a) (2.62 g, 9.05 mmol) in dry tetrahydrofuran (30 ml) was cooled under an atmosphere of argon to -78° C. n-Butyl lithium (1.5M in hexanes) (7.25 ml, 10.9 mmol) was added over 15 min and the solution stirred for a further 30 min. A solution of 1,8-dibromooctane (2.55 ml 13.6 mmol) in dry tetrahydrofuran (5 ml) was added over 10 min. The solution was stirred for 2 h, allowed to warm to room temperature and stirred for 18 h. Saturated ammonium chloride solution (30 ml) and diethyl ether (30 ml) were added and the ethereal extract was washed with brine and dried over sodium sulfate. Filtration, evaporation of the filtrate and purification by flash column chromatography (silica; 20%; ethyl acetate/hexane) to afford the product (Rf 0.43) as a white solid (2.36 g, 54%).

Workup

  1. additionwas added over 15 min
  2. stirringThe solution was stirred for 2 h
  3. stirringstirred for 18 h
  4. extractionthe ethereal extract
  5. washwas washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration, evaporation of the filtrate and purification by flash column chromatography (silica; 20%; ethyl acetate/hexane)

Sources & evidence

ORD record
ord-59b940af8d2245a78bc51e2450052ae5
Source dataset
uspto-grants-2000_06
Patent number
US06080871

Reaction notes

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