Triethylamine → 4-[6-(2,2,2-Trifluoro-acetylamino)-hexanoylamino]-benzenesulfonyl azide

HRID 1714079Notes

Reaction equation

HRID 1714079 reaction equation
[NH2:1][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.[F:21][C:22]([F:35])([F:34])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31](Cl)=[O:32])=[O:24]>CN(C)C=O>[F:21][C:22]([F:34])([F:35])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[N+:12]=[N-:13])(=[O:9])=[O:10])=[CH:4][CH:3]=1)=[O:32])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112064084-Aminobenzenesulfonyl azideHCID 114365186-(Trifluoroacetamido)hexanoyl chloride

Product 1

HCID 866261244-[6-(2,2,2-Trifluoro-acetylamino)-hexanoylamino]-benzenesulfonyl azide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 0.57 g (3 mmol) of para-amino-benzenesulfonyl azide dissolved in 5 mL dimethylformamide was added 0.9 mL (6 mmol) triethylamine, then the (2,2,2-trifluro-acetylamino)-hexanoyl chloride dissolved in 10 mL dimethylformamide was added dropwise. The mixture turned brown and was stirred under argon for 24 hrs. Solvent was evaporated, and the remaining oil was dissolved in 10 mL dichloromethane and left at room temperature for 1 hr. The precipitate was filtrated and the solution was evaporated to yield 1.10 g crude oil. The obtained compound was directly used in oligonucleotide synthesis.

Workup

  1. additionwas added dropwise
  2. customSolvent was evaporated
  3. dissolutionthe remaining oil was dissolved in 10 mL dichloromethane
  4. waitleft at room temperature for 1 hr
  5. filtrationThe precipitate was filtrated
  6. customthe solution was evaporated

Sources & evidence

ORD record
ord-223c7ad2ab5a4003b0395fa342dfae5c
Source dataset
uspto-grants-2010_09
Patent number
US07795423B2

Reaction notes

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