Propylamine → N-[3-(4-Nitro-3-propylaminomethyl-phenylsulfanyl)-phenyl]-benzenesulfonamide

HRID 390227Notes

Reaction equation

HRID 390227 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([S:12][C:13]2[CH:14]=[C:15]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])=O.[CH2:29]([NH2:32])[CH2:30][CH3:31].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>ClCCCl>[N+:9]([C:8]1[CH:7]=[CH:6][C:5]([S:12][C:13]2[CH:14]=[C:15]([NH:19][S:20]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=2)=[CH:4][C:3]=1[CH2:1][NH:32][CH2:29][CH2:30][CH3:31])([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 7852PropylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 58625048N-[3-(3-Formyl-4-nitro-phenylsulfanyl)-phenyl]-benzenesulfonamide

Product 1

HCID 58625103N-[3-(4-Nitro-3-propylaminomethyl-phenylsulfanyl)-phenyl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of N-[3-(3-formyl-4-nitro-phenylsulfanyl)-phenyl]-benzenesulfonamide (0.0027 mol), propylamine (0.003 mol) and NaBH(OAc)3 (0.0041 mol) in DCE (60 mL) was reacted overnight at room temperature. Then a 10% NaOH solution was added and the mixture was extracted with CH2Cl2. The extract was dried (MgSO4) and then purified by column chromatography over silica gel (eluent: 1:0 to 7:1 CH2Cl2:CH3OH). The product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. customwas reacted overnight at room temperature
  2. extractionthe mixture was extracted with CH2Cl2
  3. dry with materialThe extract was dried (MgSO4)
  4. custompurified by column chromatography over silica gel (eluent: 1:0 to 7:1 CH2Cl2:CH3OH)
  5. customThe product fractions were collected
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7851a53b97b746998fc9f413e0598482
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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