Sulfamide → 3-(3-{[tert-butyl(diphenyl)silyl]oxy}propyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

HRID 2237464Notes

Reaction equation

HRID 2237464 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH2:21][NH:22][CH2:23][C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH2:26])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:31](N)(N)(=[O:33])=[O:32]>COCCOCCOC>[Si:1]([O:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[NH:26][S:31]1(=[O:33])=[O:32])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 685819032-{[(3-{[Tert-butyl(diphenyl)silyl]oxy}propyl)amino]methyl}aniline

Product 1

HCID 685826103-(3-{[tert-butyl(diphenyl)silyl]oxy}propyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxideYield 95%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

A solution of 2-{[(3-{[tert-butyl(diphenyl)silyl]oxy}propyl)amino]methyl}aniline (0.45 g, 1.1 mmol) and sulfamide (0.12 g, 1.3 mmol) in diglyme (5 mL) was added dropwise to a flask containing refluxing diglyme (3 mL) over 10 minutes. The reaction mixture was stirred at reflux for 1 hour, then cooled to room temperature and evaporated to a brown oil. The crude reaction product was purified by flash chromatography (SiO2, 3-30% ethyl acetate/hexanes) to afford 3-(3-{[tert-butyl(diphenyl)silyl]oxy}propyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.50 g, 95%) as a colorless oil:

Workup

  1. additioncontaining
  2. temperatureat reflux for 1 hour
  3. customevaporated to a brown oil
  4. customThe crude reaction product
  5. customwas purified by flash chromatography (SiO2, 3-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8a8329493d614522894268782e757ac2
Source dataset
uspto-grants-2010_05
Patent number
US07718652B2

Reaction notes

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