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

HRID 637921Notes

Reaction equation

HRID 637921 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). Stir 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 10Pd/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. extractionextract 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 10Pd/C
  7. waithydrogenate at 3 atm for 4 hours
  8. filtrationFilter
  9. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-648f184acfcb4aecbe555abb6f783c62
Source dataset
uspto-grants-1985_12
Patent number
US04559340

Reaction notes

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