Triethylamine → n-Dansyl (3 aminopropanoyl) benzenesulfonyl azid

HRID 1714081Notes

Reaction equation

HRID 1714081 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[N+:12]=[N-:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:21]([NH:37][CH2:38][CH2:39][C:40](Cl)=[O:41])([C:24]1[C:36]2[CH:35]=[CH:34][CH:33]=[C:29]([N:30]([CH3:32])[CH3:31])[C:28]=2[CH:27]=[CH:26][CH:25]=1)(=[O:23])=[O:22]>CN(C)C=O>[S:21]([NH:37][CH2:38][CH2:39][C:40]([C:6]1[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=1[S:8]([N:11]=[N+:12]=[N-:13])(=[O:10])=[O:9])=[O:41])([C:24]1[C:36]2[CH:35]=[CH:34][CH:33]=[C:29]([N:30]([CH3:32])[CH3:31])[C:28]=2[CH:27]=[CH:26][CH:25]=1)(=[O:22])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112064084-Aminobenzenesulfonyl azideHCID 86626125N-Dansyl 3 aminopropanoyl chloride

Product 1

HCID 91095697n-Dansyl (3 aminopropanoyl) benzenesulfonyl azid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 152 mg (0.8 mmol) of para-amino-benzenesulfonyl azide dissolved in 5 mL dimethylformamide was added 0.11 mL (6 mmol) triethylamine, then 0.5 mmol N-Dansyl 3 aminopropanoyl chloride dissolved in 10 mL dimethylformamide was added dropwise. The mixture was stirred under argon for 24 hrs. The solvent was evaporated, the remaining oil was purified by chromatography on silica (Eluent Toluol/Aceticacidethylester 1:1). The fractions containing the product were collected and the solution was evaporated.

Workup

  1. additionwas added dropwise
  2. customThe solvent was evaporated
  3. customthe remaining oil was purified by chromatography on silica (Eluent Toluol/Aceticacidethylester 1:1)
  4. additionThe fractions containing the product
  5. customwere collected
  6. customthe solution was evaporated

Sources & evidence

ORD record
ord-d702ce3668d047bfb686bdf133293fc9
Source dataset
uspto-grants-2010_09
Patent number
US07795423B2

Reaction notes

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