Water → N-(1,1,3-trioxo-1,2,3,4-tetrahydro-1lambda6-benzo[1,2,4]thiadiazin-7-yl)-methanesulfonamide

HRID 730492Notes

Reaction equation

HRID 730492 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=1.Cl[S:14]([N:17]=[C:18]=[O:19])(=[O:16])=[O:15].[Cl-].[Al+3].[Cl-].[Cl-].O>[N+](CC)([O-])=O>[O:15]=[S:14]1(=[O:16])[C:3]2[CH:4]=[C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:7][C:2]=2[NH:1][C:18](=[O:19])[NH:17]1

Participants

6

Reactant 4

HCID 962Water2×HCID 70918Chlorosulfonyl isocyanateHCID 37325774-(Methylsulfonamido)anilineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 24858396N-(1,1,3-trioxo-1,2,3,4-tetrahydro-1lambda6-benzo[1,2,4]thiadiazin-7-yl)-methanesulfonamideYield 81%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

A solution of N-(4-amino-phenyl)-methanesulfonamide (Example 3b′, 90.7 g, 0.49 mol) in nitroethane (900 mL) was added dropwise over 1.5 h to a mechanically stirred solution of chlorosulfonylisocyanate (50.6 mL, 0.54 mol) in nitroethane (150 mL) at −20° C. The resulting suspension was stirred at −20° C. for 30 min, then aluminum chloride (77.9 g, 0.58 mol) was added in one portion over 1 min. The resulting brown solution was warmed to 25° C., and then was heated at 110° C. for 1 h (considerable gas evolution was noted during this time). After cooling to −5° C., water (300 mL) was added dropwise via addition funnel over 15 min, followed by the rapid addition of more water (700 mL). The resulting suspension was allowed to warm to 25° C. and vigorously stirred for 30 min, and then was filtered through medium paper using a Büchner funnel. The collected solid was washed with water (1×300 mL) and was air-dried to afford the desired product, N-(1,1,3-trioxo-1,2,3,4-tetrahydro-1λ6-benzo[1,2,4]thiadiazin-7-yl)-methanesulfonamide (115.2 g, 0.40 mmol, 81% yield) as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ 3.00 (3H, s), 7.22 (1H, d, J=8.5 Hz), 7.46 (1H, dd, J1=8.8 Hz, J2=2.7 Hz), 7.51 (1H, d, J=2.4 Hz), 9.92 (1H, s), 11.20 (1H, s).

Workup

  1. temperatureThe resulting brown solution was warmed to 25° C.
  2. temperaturewas heated at 110° C. for 1 h (considerable gas evolution
  3. temperatureAfter cooling to −5° C.
  4. temperatureto warm to 25° C.
  5. stirringvigorously stirred for 30 min
  6. filtrationwas filtered through medium paper
  7. washThe collected solid was washed with water (1×300 mL)
  8. customwas air-dried

Sources & evidence

ORD record
ord-38fd39fa5f634bd1839935ba63a398b3
Source dataset
uspto-grants-2009_09
Patent number
US07582754B2

Reaction notes

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