Methanesulfonic Acid → HCID 22595758, compound

HRID 2268776Notes

Reaction equation

HRID 2268776 reaction equation
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([NH:16][CH:17]([CH3:19])[CH3:18])(=[O:15])=[O:14])=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2].[CH3:20]S(O)(=O)=O.O1CCCOO1>ClCCl>[CH2:1]([S:3]([C:6]1[CH:7]=[CH:8][C:9]2[NH:12][S:13](=[O:15])(=[O:14])[N:16]([CH:17]([CH3:18])[CH3:19])[CH2:20][C:10]=2[CH:11]=1)(=[O:4])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 18332404HCID 18332404, compoundHCID 19593658CID 19593658

Product 1

HCID 22595758HCID 22595758, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N-(4-Ethylsulfonylphenyl)-N′-(1-methylethyl)sulfamide (5 g, 0.016 mol) was dissolved in dry dichloromethane (150 ml) and methanesulphonic acid (18.87 ml, 0.303 mol). The solution was cooled at 0° C. before the addition of trioxan (0.480 g, 0.005 mol) in dichloromethane (15 ml). After stirring at 0° C. for 1 hr, the reaction mixture was poured onto ice-water (250 ml), the layers separated, dried (MgSO4) and concentrated in vacuo to yield 3,4-dihydro-6-(ethylsulfonyl)-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide as a white solid. δ(1H NMR, DMSO, ppm): 1.10 (9H, m), 3.30 (2H, q), 4.10 (1H, m), 4.80 (2H, s), 6.95 (1H, d), 7.75 (1H, dd), 7.80 (1H, d).

Workup

  1. additionthe reaction mixture was poured onto ice-water (250 ml)
  2. customthe layers separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63a0404d961b497d9c4bf7a75b9c2046
Source dataset
uspto-grants-2001_12
Patent number
US06329366B1

Reaction notes

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