N-Butyl-N-nitrosobutyramide → Jeffamine

HRID 1074128Notes

Reaction equation

HRID 1074128 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

5

Reactant 3

HCID 149617N-Butyl-N-nitrosobutyramideHCID 15131492JeffamineHCID 21923999Chloroform methanol acetic acid water

Product 2

HCID 15131492JeffamineHCID 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.

Workup

  1. dry with materialin very dry (high purity) solvents (ANP-EAC-NOS in dry tetrahydrofuran, BBA-NOS in dry dioxane
  2. customAfter 16 hours of reaction at room temperature in the dark
  3. extractionMonosubstituted Jeffamine derivatives were extracted with the TLC solvent
  4. customto remove the residual acetic acid

Sources & evidence

ORD record
ord-673b1742801c4b41a591ca677c9f3b75
Source dataset
uspto-grants-1990_11
Patent number
US04973493

Reaction notes

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