Chlorotrimethylsilane → HCID 18957723, compound

HRID 2379146Notes

Reaction equation

HRID 2379146 reaction equation
Cl.[OH:2][CH2:3][C:4]1[N:5]=[CH:6][NH:7][C:8]=1[CH3:9].C(N(CC)CC)C.[CH3:17][Si:18](Cl)([CH3:20])[CH3:19].[CH3:22][N:23]([CH3:28])[S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:22][N:23]([CH3:28])[S:24]([N:7]1[C:8]([CH3:9])=[C:4]([CH2:3][O:2][Si:18]([CH3:20])([CH3:19])[CH3:17])[N:5]=[CH:6]1)(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 30847074-Methylimidazol-5-ylmethanolhydrochloride

Product 1

HCID 18957723HCID 18957723, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-(hydroxymethyl)-5-methylimidazole hydrochloride (14.9 g) in dry dichloromethane (500 ml) containing triethylamine (50 g) was treated with trimethylsilyl chloride (21.7 g) and the reaction mixture was stirred at room temperature overnight. Dimethylsulphamoyl chloride (14.3 g) was added and the reaction mixture was again stirred at room temperature overnight. The resulting suspension was filtered and the collected solid was washed with dichloromethane (100 ml). The filtrate was concentrated onto silica and purification by FCC eluting with hexane:ether (4:1) gave the title compound as an oil (7.2 g), t.l.c. (ether) Rf 0.5.

Workup

  1. stirringthe reaction mixture was again stirred at room temperature overnight
  2. filtrationThe resulting suspension was filtered
  3. washthe collected solid was washed with dichloromethane (100 ml)
  4. concentrationThe filtrate was concentrated onto silica and purification by FCC
  5. washeluting with hexane:ether (4:1)

Sources & evidence

ORD record
ord-ed54e8a6cd7c4868a57d7f8089b9894f
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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