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

HRID 390283Notes

Reaction equation

HRID 390283 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([S:12]([C:14]2[CH:15]=[C:16]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])=O.[CH2:30]([NH2:33])[CH2:31][CH3:32].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[N+:9]([C:8]1[CH:7]=[CH:6][C:5]([S:12]([C:14]2[CH:15]=[C:16]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:22])=[O:23])[CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:4][C:3]=1[CH2:1][NH:33][CH2:30][CH2:31][CH3:32])([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 7852PropylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58625065N-[3-(3-Formyl-4-nitro-benzenesulfinyl)-phenyl]-benzenesulfonamide

Product 1

HCID 58625145N-[3-(4-Nitro-3-propylaminomethyl-benzenesulfinyl)-phenyl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The following reaction was run under N2. A mixture of N-[3-(3-formyl-4-nitro-benzenesulfinyl)-phenyl]-benzenesulfonamide (0.0023 mol) and propylamine (0.0025 mol) in DCE (50 mL) was stirred at room temperature and NaBH(OAc)3 (0.8 g) was added. The reaction mixture was stirred overnight at room temperature, and then a NaHCO3 solution was added. The organic layer was separated, dried, and filtered, and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. customThe following reaction
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8da106186c1048bca9cbb039d1135ff4
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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