Dimethylformamide → N-[[2'-[(t-butylamino)sulfonyl]-1,1'-biphenyl-4-yl]methyl]-N-heptylamine

HRID 492292Notes

Reaction equation

HRID 492292 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Br)=[CH:17][CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:23]([NH2:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:30][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:17][CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81271-HeptanamineHCID 11430Potassium CarbonateHCID 15282100[2'-(N-t-Butylsulfamoyl)biphenyl-4-yl]methyl bromide

Product 1

HCID 68851407N-[[2'-[(t-butylamino)sulfonyl]-1,1'-biphenyl-4-yl]methyl]-N-heptylamineYield 42.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

[[2′-[(t-Butylamino)sulfonyl]-1,1′-biphenyl-4-yl]methyl] bromide (0.94 g), n-heptylamine (0.28 g) and potassium carbonate (0.35 g) were added to dimethylformamide and the mixture was stirred at room temperature. Sixteen hours and 30 minutes later, ethyl acetate (30 mL) was added, and the resulting mixture was washed three times with brine (100 mL, each). The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column (chloroform/ethyl acetate) to afford N-[[2′-[(t-butylamino)sulfonyl]-1,1′-biphenyl-4-yl]methyl]-N-heptylamine as a yellow oil (0.43 g). Yield: 42%.

Workup

  1. washthe resulting mixture was washed three times with brine (100 mL
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c2888e3bd8b74dd4b431bb36f547b667
Source dataset
uspto-grants-2009_05
Patent number
US07531576B2

Reaction notes

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