Oxalyl chloride → N-Dansyl 3 aminopropanoyl chloride

HRID 1714080Notes

Reaction equation

HRID 1714080 reaction equation
[S:1]([NH:17][CH2:18][CH2:19][C:20]([OH:22])=O)([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2].C(Cl)(=O)C([Cl:26])=O>ClCCl.CN(C)C=O>[S:1]([NH:17][CH2:18][CH2:19][C:20]([Cl:26])=[O:22])([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 688460N-[[5-(Dimethylamino)-1-naphthalenyl]sulfonyl]-beta-alanine

Product 1

HCID 86626125N-Dansyl 3 aminopropanoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

970 mg(3 mmol) dansyl beta alanin were dissolved in 5 mL dried dichloromethane and stirred under argon flux at 0° C. Then 0.6 mL (6.6 mmol) oxalyl chloride was added drop wise at 0° C., and subsequently, a few drops of dried dimethylformamide were added which lead to gas development. The mixture was stirred at room temperature for 100 min. The solvents were removed by using a rotary evaporator and then the remainder was twice evaporated with dichloromethane. The crude product was used directly in the next step.

Workup

  1. stirringThe mixture was stirred at room temperature for 100 min
  2. customThe solvents were removed
  3. customa rotary evaporator
  4. customthe remainder was twice evaporated with dichloromethane

Sources & evidence

ORD record
ord-0bc429fe9c9b438aa76af87323eff686
Source dataset
uspto-grants-2010_09
Patent number
US07795423B2

Reaction notes

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