Triethylamine → Chlorosulfamic acid

HRID 583085Notes

Reaction equation

HRID 583085 reaction equation
[Cl:1][S:2]([N:5]=[C:6]=O)(=[O:4])=[O:3].[CH2:8]([C:11]1(C=[CH:16][CH:15]=[CH:14][CH2:13]1)[NH2:12])[CH:9]=[CH2:10].C([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])C.[S:25](Cl)(=[O:28])(=[O:27])N>C(#N)C.O>[S:2]([Cl:1])(=[O:4])(=[O:3])[NH2:5].[CH3:10][CH2:9][CH2:8][CH:11]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:24][C:23]=2[N:20]([CH2:21][CH:22]=[CH2:6])[S:25](=[O:28])(=[O:27])[NH:12]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 70918Chlorosulfonyl isocyanateHCID 86754291HCID 86754291, compound

Product 2

HCID 24499Chlorosulfamic acidHCID 17777142HCID 17777142, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
2.5 °C

Procedure

Sulfamoyl chloride was prepared in situ by cautiously adding to a solution of chlorosulfonyl isocyanate (7.05 g, 0.05 mol) in acetonitrile (50 ml) cooled to 0-5° C., water (0.9 ml) in acetonitrile (5 ml) keeping the temperature below 10° C., whilst stirring for 1 hour. A solution of 1-(prop-2-en-1-yl) aniline (6.65 g, 0.05 mol) and triethylamine (5.05 g, 0.05 mol) was stirred at 0-5° C. and the sulfamoyl chloride prepared above was added slowly keeping the temperature below 10° C., stirring overnight. The reaction was poured into ice-water(100 ml) and the product, 1-phenyl-1-(prop-2-en-1-yl) sulfamide was collected by filtration. This was treated with 2-methylpropionaldehyde and methane sulfonic acid as described previously to give 3,4-dihydro-4-(2-methylethyl)-1-(prop-2-en-1-yl)-1H-2,1,3-benzothiadiazine-2,2-dioxide. This compound was converted to 3,4-dihydro-4-(2-methylethyl)-1-(2-oxoethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide by methods discussed previously.

Workup

  1. customthe temperature below 10° C.
  2. additionabove was added slowly
  3. customthe temperature below 10° C.
  4. stirringstirring overnight
  5. filtrationthe product, 1-phenyl-1-(prop-2-en-1-yl) sulfamide was collected by filtration
  6. additionThis was treated with 2-methylpropionaldehyde and methane sulfonic acid

Sources & evidence

ORD record
ord-17fd0fd7ff7644f3916a3a6bc0d80c88
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Reaction notes

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