Dichloromethane → HCID 22595758, compound

HRID 1760524Notes

Reaction equation

HRID 1760524 reaction equation
CSC1[CH:8]=[CH:7][C:6]([NH:9][S:10]([NH:13][CH:14]([CH3:16])[CH3:15])(=[O:12])=[O:11])=[CH:5][CH:4]=1.[CH3:17][S:18]([OH:21])(=O)=[O:19].O1C[CH2:26][CH2:25]OO1.Cl[CH2:29]Cl>>[CH2:25]([S:18]([C:17]1[CH:8]=[CH:7][C:6]2[NH:9][S:10](=[O:11])(=[O:12])[N:13]([CH:14]([CH3:15])[CH3:16])[CH2:29][C:5]=2[CH:4]=1)(=[O:21])=[O:19])[CH3:26]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 6395Methanesulfonic AcidHCID 19593658CID 19593658HCID 54434743N-[4-(Methylsulfanyl)phenyl]-N'-propan-2-ylsulfuric diamide

Product 1

HCID 22595758HCID 22595758, compound

Conditions

Temperature
0 °C

Procedure

N-(4-Methylthiophenyl)-N′-(1-methylethyl)sulfamide (4.35 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): 0.9 (6H, d), 2.3 (3H, s), 3.9 (1H, m), 4.5 (2H, s), 6.6 (1H, d), 7.0 (2H, m), 10.1 (1H, s)

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-c262fa680e9a43cbaf53f21acd125cd0
Source dataset
uspto-grants-2005_01
Patent number
US06844338B2

Reaction notes

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