Propylamine → HCID 58625170, compound

HRID 390213Notes

Reaction equation

HRID 390213 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27])[O:6][C:7]1[CH:8]=[C:9]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:10]=[CH:11][CH:12]=1)=O.[CH2:29]([NH2:32])[CH2:30][CH3:31].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[N+:26]([C:25]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:8]=[C:9]([NH:13][S:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)(=[O:15])=[O:16])[CH:10]=[CH:11][CH:12]=2)=[CH:4][C:3]=1[CH2:1][NH:32][CH2:29][CH2:30][CH3:31])([O-:28])=[O:27]

Participants

6

Reactant 4

HCID 7852PropylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58625131HCID 58625131, compound

Product 1

HCID 58625170HCID 58625170, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Under N2, a mixture of N-[3-(3-formyl-4-nitrophenoxy)-phenyl]-benzenesulfonamide (0.0060 mol) and propylamine (0.0085 mol) in DCE (50 mL) was stirred at room temperature, then NaBH(OAc)3 (0.0080 mol) was added and the reaction mixture was stirred overnight at room temperature. A saturated NaHCO3 solution (50 mL) was added and the layers were separated. The organic layer was dried, filtered off and the solvent was evaporated. The residue was purified over silica gel filter (eluent: 98:2 CH2Cl2:CH3OH). The purest product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. customthe layers were separated
  3. customThe organic layer was dried
  4. filtrationfiltered off
  5. customthe solvent was evaporated
  6. customThe residue was purified over silica gel
  7. filtrationfilter (eluent: 98:2 CH2Cl2:CH3OH)
  8. customThe purest product fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-048f80b761724ef9b4b3a3e9bf3e4960
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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