Sodium Azide → 2-(2-Aminoethyl)-6-chloro-3,4-dihydro-1,1-dioxo-7-sulfamoyl-1,2,4-benzothiadiazine

HRID 868206

Reaction equation

HRID 868206 reaction equation
Br[CH2:2][CH2:3][N:4]1[CH2:9][NH:8][C:7]2[CH:10]=[C:11]([Cl:18])[C:12]([S:14](=[O:17])(=[O:16])[NH2:15])=[CH:13][C:6]=2[S:5]1(=[O:20])=[O:19].[N-:21]=[N+]=[N-].[Na+]>CN(C=O)C>[NH2:21][CH2:2][CH2:3][N:4]1[CH2:9][NH:8][C:7]2[CH:10]=[C:11]([Cl:18])[C:12]([S:14](=[O:17])(=[O:16])[NH2:15])=[CH:13][C:6]=2[S:5]1(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 142809712-(2-Bromoethyl)-6-chloro-3,4-dihydro-1,1-dioxo-7-sulfamoyl-1,2,4-benzothiadiazine

Product 1

HCID 142809722-(2-Aminoethyl)-6-chloro-3,4-dihydro-1,1-dioxo-7-sulfamoyl-1,2,4-benzothiadiazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine the product of step A (12.2 g) with sodium azide (3.9 g) in DMF (200 ml). Stirr 44 hours, extract with ethyl acetate, wash with water, dry the organic layer over MgSO4 and concentrate. Dissolve the resultant residue in ethanol (150 ml), add 5.0 g 10% Pd/C and hydrogenate at 3 atm for 4 hours. Filter and concentrate the filtrate to obtain 2-(2-aminoethyl)-6-chloro-3,4-dihydro-1,1-dioxo-7-sulfamoyl-1,2,4-benzothiadiazine.

Workup

  1. extractionStirr 44 hours, extract with ethyl acetate
  2. washwash with water
  3. dry with materialdry the organic layer over MgSO4
  4. concentrationconcentrate
  5. dissolutionDissolve the resultant residue in ethanol (150 ml)
  6. additionadd 5.0 g 10% Pd/C
  7. filtrationFilter
  8. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-f17d98bf8e16441da44ba062bc71e775
Source dataset
uspto-grants-1988_10
Patent number
US04778795

Linked notes

Loading…