Sulfamide → 5-fluoro-3-(1-methylethyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine-2,2-dioxide

HRID 583079Notes

Reaction equation

HRID 583079 reaction equation
[CH3:1][CH:2]([NH:4][CH2:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:13])[CH3:3].[S:14](N)(N)(=[O:16])=[O:15]>N1C=CC=CC=1>[F:12][C:11]1[C:6]2[CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[S:14](=[O:16])(=[O:15])[NH:13][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 17777127N-(1-methylethyl)-(2-amino-6-fluorophenyl)methylamine

Product 1

HCID 177771315-fluoro-3-(1-methylethyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine-2,2-dioxide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
115 °C

Procedure

N-(1-methylethyl)-(2-amino-6-fluorophenyl)methylamine (0.3 g, 1.6 mmol) and sulphamide (5.08 g, 2.5 mmol) were suspended in 7 ml of dry pyridine and the mixture stirred at 115° C. for 24 hours in argon atmosphere. After cooling at room temperature the solvent was removed in vacuo and the residue dissolved in EtOAc (50 ml) and washed with 5N HCl (2×50 ml). Solvents removal afforded 5-fluoro-3-(1-methylethyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine-2,2-dioxide as a pale yellow solid.

Workup

  1. temperatureAfter cooling at room temperature the solvent
  2. customwas removed in vacuo
  3. dissolutionthe residue dissolved in EtOAc (50 ml)
  4. washwashed with 5N HCl (2×50 ml)
  5. customSolvents removal

Sources & evidence

ORD record
ord-347b6f424b7a44848c21b0fb89d90e76
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Reaction notes

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