Sulfamide → HCID 68581770, compound

HRID 2237513Notes

Reaction equation

HRID 2237513 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][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[CH2:4][C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=2[NH:1][S:17]1(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 66387431HCID 66387431, compound

Product 1

HCID 68581770HCID 68581770, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A solution of N-(2-aminobenzyl)-2-fluoroaniline (4.3 g, 20 mmol) in diglyme (50 mL) was treated with sulfamide (2.5 g, 26 mmol) and heated to reflux for 0.5 h. The reaction mixture was evaporated and the oily residue purified by flash chromatography (SiO2, 10-100% ethyl acetate/hexanes) to provide 3-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (3.0 g) as a tan solid:

Workup

  1. temperatureheated
  2. temperatureto reflux for 0.5 h
  3. customThe reaction mixture was evaporated
  4. customthe oily residue purified by flash chromatography (SiO2, 10-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ca312189f84b4e0ca32a290e4b52b39b
Source dataset
uspto-grants-2010_05
Patent number
US07718652B2

Reaction notes

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