Sodium Hydroxide → HCID 22462212, compound

HRID 322482Notes

Reaction equation

HRID 322482 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([CH:23]1[CH2:32][CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]1)=[O:22])(=[O:12])=[O:11])([O-])=O.[Sn](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>C(O)(=O)C.Cl.O>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([CH:23]1[CH2:32][CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]1)=[O:22])(=[O:12])=[O:11]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 22462213HCID 22462213, compound

Product 1

HCID 22462212HCID 22462212, compoundYield 95.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 1,2,3,4-Tetrahydro-2-naphthalencarboxylic acid[6- (2-nitrobenzenesulfonylamino)-hexyl]-amide (0.54 g, 1.17 mmol) in 5 mL of glacial acetic acid stirred at 0° C. was added a solution of tin chloride (1.32 g, 5.88 mmol)in 5 mL conc. HCl and 1 mL of water. The reaction mixture was warmed to room temperature and stirred for 3 h and poured over crushed ice (50 g). The reaction mixture was neutralized with 10% sodium hydroxide and extracted with chloroform (5×50 mL), dried over sodium sulfate and concentrated to afford yellow oil (0.48 g, 95%).

Workup

  1. additionpoured
  2. extractionextracted with chloroform (5×50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-63e096888f0a4f3aab7387932d76c5cf
Source dataset
uspto-grants-2001_04
Patent number
US06211241B1

Reaction notes

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