Sulfamic Acid → HCID 68708401, compound

HRID 1818827Notes

Reaction equation

HRID 1818827 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([NH2:16])=[CH:12][CH:13]=[CH:14][CH:15]=1.[S:17](N)(N)(=[O:19])=[O:18].S(=O)(=O)(O)N>COCCOCCOC>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][S:17]1(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 5987Sulfamic AcidHCID 82267SulfamideHCID 29067503HCID 29067503, compound

Product 1

HCID 68708401HCID 68708401, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

A solution of N-(2-fluoro-4-methylphenyl)benzene-1,2-diamine (3.9 g, 18 mmol) in diglyme (36 mL) was treated with sulfamide (2.1 g, 22 mmol) and added dropwise over 10 min to a refluxing solution of sulfamic acid (0.9 g, 9 mmol) in diglyme (36 mL), and the reaction mixture was kept at reflux for an additional 15 minutes, then cooled to room temperature and concentrated. The residue was dissolved in ethyl ether (300 mL), washed with 2 N hydrochloric acid (100 mL), evaporated, and flash chromatographed (SiO2, 050% ethyl acetate/hexanes) provided 1-(2-fluoro-4-methylphenyl)-1,3-dihydro-2,1,3-benzothiadiazole2,2-dioxide (2.6 g) as a red solid:

Workup

  1. temperatureat reflux for an additional 15 minutes
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl ether (300 mL)
  4. washwashed with 2 N hydrochloric acid (100 mL)
  5. customevaporated
  6. customflash chromatographed (SiO2, 050% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7c098893dc354b92872551aa1ccb9b0a
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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