Sulfamide → HCID 66898896, compound

HRID 2168543Notes

Reaction equation

HRID 2168543 reaction equation
[NH2:1][C:2]1[C:3]([NH:12][CH2:13][CH:14]([O:17][CH3:18])[O:15][CH3:16])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[S:19](=[O:23])(=[O:22])(N)N>COCCOCCOC>[CH3:16][O:15][CH:14]([O:17][CH3:18])[CH2:13][N:12]1[C:3]2[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=[CH:11][C:2]=2[NH:1][S:19]1(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 66889618HCID 66889618, compound

Product 1

HCID 66898896HCID 66898896, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

A solution of methyl 3-amino-2-(2,2-dimethoxyethylamino)benzoate (0.5 g, 2.0 mmol) from Step C above and sulfuric diamide (0.2 g, 2.4 mmol) in diglyme (2 mL) was added to boiling diglyme (5 mL) dropwise and continued to reflux for 35 min. The flask was cooled to room temperature and the solvent was removed in vacuo. The crude reaction was purified by column chromatography (silica gel, 0% to 100% ethyl acetate in hexanes) to afford methyl 3-(2,2-dimethoxyethyl)-1,3-dihydro-2,1,3-benzothiadiazole-4-carboxylate 2,2-dioxide (0.2 g, 27%): 1H NMR (500 MHz, DMSO-d6) δ 7.08 (br s, 1H), 6.59 (dd, J=8.0, 1.5 Hz, 1H), 6.52 (t, J=8.0 Hz, 1H), 6.46 (dd, J=6.0, 1.5 Hz, 1H), 4.41 (t, J=5.0 Hz, 1H), 3.82 (d, J=5.0 Hz, 2H), 3.74 (s, 3H), 3.14 (s, 6H).

Workup

  1. temperatureto reflux for 35 min
  2. customthe solvent was removed in vacuo
  3. customThe crude reaction
  4. customwas purified by column chromatography (silica gel, 0% to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9ff46011150d4fc5af63ec73f6dd655b
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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