Sulfamide → 3-Methyl-3,4-dihydro-1H-2,1,3-benzothiadiazine-2,2dioxide

HRID 1720026Notes

Reaction equation

HRID 1720026 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][NH:5][CH3:6].[S:11](N)(N)(=[O:13])=[O:12]>N1C=CC=CC=1>[CH3:6][N:5]1[CH2:4][C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[NH:1][S:11]1(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 118154102-[(Methylamino)methyl]aniline

Product 1

HCID 177771553-Methyl-3,4-dihydro-1H-2,1,3-benzothiadiazine-2,2dioxide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-N-methyl-benzylamine (3.7 g;27mmol) and sulfamide (5.2 g: 54 mmol) were dissolved in pyridine (40 ml). Mixture was refluxed for 3 hours, then the solvent was removed in vacuo, and water (50 ml) was added. Reaction mixture was extracted with ethyl acetate. Extract was dried over magnesium sulfate and solvent was evaporated off. Crude product was recrystallized from chloroform-hexane, to give the product, (4.4 g).

Workup

  1. temperatureMixture was refluxed for 3 hours
  2. customthe solvent was removed in vacuo, and water (50 ml)
  3. additionwas added
  4. customReaction mixture
  5. extractionwas extracted with ethyl acetate
  6. extractionExtract
  7. dry with materialwas dried over magnesium sulfate and solvent
  8. customwas evaporated off
  9. customCrude product was recrystallized from chloroform-hexane
  10. customto give the product, (4.4 g)

Sources & evidence

ORD record
ord-e7b6e6b46a8a4795abdfdd1f52d0418c
Source dataset
uspto-grants-1996_04
Patent number
US05504095

Reaction notes

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