Sulfamide → 1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

HRID 2237488Notes

Reaction equation

HRID 2237488 reaction equation
[NH2:1][CH2:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12].[S:17](N)(N)(=[O:19])=[O:18]>COCCOCCOC>[F:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[N:5]1[C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]=2[CH2:2][NH:1][S:17]1(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 685842802-(aminomethyl)-N-(2-fluorophenyl)aniline

Product 1

HCID 685811711-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxideYield 70%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A solution of 2-(aminomethyl)-N-(2-fluorophenyl)aniline (2.07 g, 9.6 mmol) and sulfamide (1.1 g, 11.5 mmol) in digylyme (10 mL) was added to a flask containing refluxing diglyme (15 mL) over 10 min. The reaction mixture was stirred at reflux for 1 h, then cooled to room temperature and was evaporated to a brown oil. The crude reaction product was purified by flash chromatography (SiO2, 3-50% ethyl acetate/heptane) to afford 1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (1.86 g, 70%) as a white solid:

Workup

  1. additioncontaining
  2. temperatureat reflux for 1 h
  3. customwas evaporated to a brown oil
  4. customThe crude reaction product
  5. customwas purified by flash chromatography (SiO2, 3-50% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-321e8cfdf0f7418db7a6cfd8b19a9232
Source dataset
uspto-grants-2010_05
Patent number
US07718652B2

Reaction notes

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