Dichloromethane → HCID 12974659, compound

HRID 1618815Notes

Reaction equation

HRID 1618815 reaction equation
[S:1](Cl)([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].ClCCl.C(N(CC)CC)C.[CH2:28]([NH2:31])[C:29]#[CH:30]>O1CCCC1>[S:1]([NH:31][CH2:28][C:29]#[CH:30])([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

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 11801Dansyl chlorideHCID 239041Propargylamine

Product 1

HCID 12974659HCID 12974659, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

234 mg of dansyl chloride (0.87 mmol) and 4.0 mL of anhydrous dichloromethane were placed in a 25 mL round-bottom flask equipped with a CaCl2 trap. 240 μL of triethylamine (1.73 mmol) and 330 μL of propargylamine (5.20 mmol) were added to the solution, which was then kept under stirring for 12 hours at room temperature. The residue obtained by distillation under reduced pressure was redissolved in some mL of tetrahydrofuran and the resulting mixture was filtrated. The evaporation of the solvent of the filtrated solution under reduced pressure affords the product in quantitative yield.

Workup

  1. customequipped with a CaCl2 trap
  2. customThe residue obtained by distillation under reduced pressure
  3. filtrationthe resulting mixture was filtrated
  4. customThe evaporation of the solvent of the filtrated solution under reduced pressure
  5. customaffords the product in quantitative yield

Sources & evidence

ORD record
ord-a5fc838b387c4a628f05e54b52d56565
Source dataset
uspto-grants-2014_07
Patent number
US08771642B2

Reaction notes

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