2-Chloro-N-(2-hydroxyethyl)-5-nitro-benzenesulfonamide → 8-Amino-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepine 1,1-Dioxide

HRID 893811Notes

Reaction equation

HRID 893811 reaction equation
[N+](C1C=COC2C=1S(=O)(=O)NCC2)([O-])=O.Cl[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:18]=1[S:26]([NH:29][CH2:30][CH2:31][OH:32])(=[O:28])=[O:27].[H][H]>CO.[Ni]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]2[O:32][CH2:31][CH2:30][NH:29][S:26](=[O:28])(=[O:27])[C:18]=2[CH:19]=1

Participants

6

Reactant 3

HCID 145740892-Chloro-N-(2-hydroxyethyl)-5-nitro-benzenesulfonamideHCID 679076548-nitro-3,4-dihydro-(2H)-5,1,2-benzoxathiazine 1,1-dioxideHCID 178418361HCID 178418361, compound

Product 1

HCID 145740918-Amino-3,4-dihydro-2H-benzo[b][1,4,5]oxathiazepine 1,1-Dioxide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

244 g of 8-nitro-3,4-dihydro-(2H)-5,1,2-benzoxathiazine 1,1-dioxide, which is accessible by an intramolecular condensation reaction from 2-chloro-5-nitro-N-(2-hydroxyethyl)-benzenesulphonamide (DOS (German Published Specification) 1,670,759), are suspended in 600 ml of methanol and are reduced in the presence of 3 g of freshly prepared Raney nickel as catalyst by injecting three times the equimolar amount of hydrogen in an autoclave at 50° C. When the reduction is complete, the catalyst is removed from the hot reaction solution, from which the amino compound crystallizes out in fine flakes after cooling to 0° C. 205 g of 8-amino-3,4-dihydro-(2H)-5,1,2-benzoxathiazepine 1,1-dioxide of the formula ##STR17## melting point 179° C. are obtained after filtering off with suction and drying.

Workup

  1. customat 50° C
  2. customthe catalyst is removed from the hot reaction solution, from which the amino compound
  3. customcrystallizes out in fine flakes

Sources & evidence

ORD record
ord-f9e1ab10c6454689869ea85f1d34e0d8
Source dataset
uspto-grants-1992_06
Patent number
US05126481

Reaction notes

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