Sulfamide → HCID 66898896, compound

HRID 2369921Notes

Reaction equation

HRID 2369921 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-d736c3be51ca48f0a08be74096d29373
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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