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Hydrochloric Acid → 4-(2-Amino-ethyl)-N-(5-isopropyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide hydrochloride

HRID 2266396
Notes
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Reaction equation

HRID 2266396 reaction equation
[CH:1]([C:4]1[S:8][C:7]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][NH:21]C(=O)C)=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[N:6][N:5]=1)([CH3:3])[CH3:2].[ClH:25]>>[ClH:25].[NH2:21][CH2:20][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([S:10]([NH:9][C:7]2[S:8][C:4]([CH:1]([CH3:3])[CH3:2])=[N:5][N:6]=2)(=[O:12])=[O:11])=[CH:14][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 13813271N-{2-[4-(5-Isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-ethyl}-acetamide

Product 1

HCID 687820324-(2-Amino-ethyl)-N-(5-isopropyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide hydrochloride

Procedure

16.8 g N-{2-[4-(5-Isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-ethyl}-acetamide was suspended in 120 ml one molar hydrochloric acid and heated under reflux for six hours. The cooled reaction mixture was evaporated in vacuo. The resulting residue was dissolved in 300 ml ethanol and dried over MgSO4. The ethanol was removed in vacuo to obtain 21.0 g 4-(2-Amino-ethyl)-N-(5-isopropyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide hydrochloride as an amorphous solid, impurified with salts. This material was used without further purification.

Workup

  1. temperatureheated
  2. temperatureunder reflux for six hours
  3. customThe cooled reaction mixture
  4. customwas evaporated in vacuo
  5. dissolutionThe resulting residue was dissolved in 300 ml ethanol
  6. dry with materialdried over MgSO4
  7. customThe ethanol was removed in vacuo

Sources & evidence

ORD record
ord-932bab4d7bbe46eca2a14be56c152073
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07858647B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes