Tosylchloramide → HCID 12030321, compound

HRID 1510144Notes

Reaction equation

HRID 1510144 reaction equation
[CH3:1][Si:2]1([CH3:7])[CH2:6][CH:5]=[CH:4][CH2:3]1.[Br-].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[CH3:41][C:42]1[CH:43]=[CH:44][C:45]([S:48]([NH:51]Cl)(=[O:50])=[O:49])=[CH:46][CH:47]=1>C(#N)C>[CH3:1][Si:2]1([CH3:7])[CH2:6][CH:5]2[CH:4]([N:51]2[S:48]([C:45]2[CH:46]=[CH:47][C:42]([CH3:41])=[CH:43][CH:44]=2)(=[O:49])=[O:50])[CH2:3]1

Participants

5

Reactant 3

HCID 31388TosylchloramideHCID 1400231,1-Dimethyl-2,5-dihydro-1H-siloleHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 12030321HCID 12030321, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1,1-dimethyl-2,5-dihydro-1H-silole (3.0 g, 26.7 mmol) in acetonitrile (50 mL) was added phenyltrimethylammonium tribromide (1.0 g, 2.67 mmol) and chloramine-T (6.69 g, 29.4 mmol). After stirring at rt overnight the reaction mixture was filtered though a pad of Celite and concentrated under vacuum. Purification by silica gel chromatography (20% EtOAc/hexanes) afforded the desired product.

Workup

  1. filtrationwas filtered though a pad of Celite
  2. concentrationconcentrated under vacuum
  3. customPurification by silica gel chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2606bbb0f4474118840da34281b5e745
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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