N-Butyl-N-nitrosobutyramide → Jeffamine

Reaction equation

[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([N:11]=[O:12])[C:6]([CH2:8][CH2:9][CH3:10])=[O:7].[CH3:13][CH:14]([NH2:29])[CH2:15][O:16][CH2:17][CH:18]([O:20][CH2:21][CH:22]([O:24][CH2:25][CH:26]([NH2:28])[CH3:27])[CH3:23])[CH3:19].C(Cl)(Cl)Cl.CO.O.C(O)(=O)C>>[CH3:13][CH:14]([NH2:29])[CH2:15][O:16][CH2:17][CH:18]([O:20][CH2:21][CH:22]([O:24][CH2:25][CH:26]([NH2:28])[CH3:27])[CH3:23])[CH3:19].[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([N:11]=[O:12])[C:6]([CH2:8][CH2:9][CH3:10])=[O:7].[CH3:13][CH:14]([NH2:29])[CH2:15][O:16][CH2:17][CH:18]([O:20][CH2:21][CH:22]([O:24][CH2:25][CH:26]([NH2:28])[CH3:27])[CH3:23])[CH3:19]

Participants

Reactant 3

HCID 149617N-Butyl-N-nitrosobutyramide

HCID 15131492Jeffamine

HCID 21923999Chloroform methanol acetic acid water

Product 2

HCID 15131492Jeffamine

HCID 131716719nBBA Jeffamine

Procedure

Polyoxypropylenepolyamines and polyoxyethylenepolyamines (referred to as "Jeffamines", a trademark of Jefferson Chemical Co., Inc.) were photolabeled by coupling the N-oxysuccinimide ("NOS") esters of ANP-EACA, BBA and nBBA to the polymers. These NOS-derivatives were added in 0.5X amounts to 1X Jeffamine in very dry (high purity) solvents (ANP-EAC-NOS in dry tetrahydrofuran, BBA-NOS in dry dioxane or dimethylformamide and nitro BBA-NOS in dry dioxane or dimethylformamide). After 16 hours of reaction at room temperature in the dark, the products were isolated by TLC in 85/15/1/1/ chloroform/methanol/H2O/acetic acid. Monosubstituted Jeffamine derivatives were extracted with the TLC solvent and azeotrophed with water to remove the residual acetic acid. The water soluble products ANP-EAC-Jeffamine, BBA-Jeffamine, and nBBA-Jeffamine were isolated in 15%, 10% and 12% yields, respectively.