Benzenesulfonyl chloride → N,N-bis(2-trimethylsilyloxyethyl)benzenesulfonamide

HRID 2838

Reaction equation

HRID 2838 reaction equation
[CH3:1][Si:2]([O:5][CH2:6][CH2:7][NH:8][CH2:9][CH2:10][O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])([CH3:4])[CH3:3].C(N(CC)CC)C.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1C=CC=CC=1>[CH3:13][Si:12]([CH3:15])([CH3:14])[O:11][CH2:10][CH2:9][N:8]([CH2:7][CH2:6][O:5][Si:2]([CH3:1])([CH3:3])[CH3:4])[S:29]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 303242-((Trimethylsilyl)oxy)-N-(2-((trimethylsilyl)oxy)ethyl)ethanamine

Product 1

HCID 18935901N,N-bis(2-trimethylsilyloxyethyl)benzenesulfonamideYield 88%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 4.97 g of bis(2-trimethylsilyloxylethyl)amine, 3.03 g of triethylamine and 50 ml of benzene, 3.21 g of benzenesulfonyl chloride was added at 0° C. under stirring. After the addition, the mixture was taken out of the cooling bath and stirred further for 2 hours. The reaction mixture was filtered, mixture was taken out of the cooling bath and stirred further for 2 hours. The reaction mixture was filtered, and the filtrate was subjected to vacuum distillation. The residue was passed through a silica gel column with the eluent varying from benzene to benzen-acetic acid (9:1). As a result, 6.23 g of the title compound was obtained as a colorless oily substance. NMRδ: 7.83 (2H,d,J=8.0 Hz),7.52 (3H,m), 3.72, 3.31 (each 4H,t,J=6.5 Hz), 0.09 (18H,s)

Workup

  1. additionwas added at 0° C.
  2. additionAfter the addition
  3. stirringstirred further for 2 hours
  4. filtrationThe reaction mixture was filtered
  5. stirringstirred further for 2 hours
  6. filtrationThe reaction mixture was filtered
  7. distillationthe filtrate was subjected to vacuum distillation

Sources & evidence

ORD record
ord-ee33145d3712452584d543409e62c64a
Source dataset
uspto-grants-1998_03
Patent number
US05730953

Linked notes

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