Triethylamine → HCID 58124933, compound

HRID 1971666Notes

Reaction equation

HRID 1971666 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]#[C:7][CH2:8][S:9][CH2:10][CH2:11][OH:12].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(OCC)C>[CH3:20][S:21]([O:12][CH2:11][CH2:10][S:9][CH2:8][C:7]#[C:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58124823HCID 58124823, compound

Product 1

HCID 58124933HCID 58124933, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1.28 g of 9c and 1.5 ml of triethyl amine in 10 ml of diethyl ether was treated at 0° C. with 0.78 g of methanesulphonyl chloride in 5 ml of diethyl ether. The reaction mixture was stirred for ½ h and then quenched by addition of 20 ml of water. The product was extracted into ethyl acetate and the combined extracts were washed once with 1M K2CO3 and once with water, dried and concentrated, to provide 1.7 g as essentially pure 9d and was used without further purification in the next step.

Workup

  1. customquenched by addition of 20 ml of water
  2. extractionThe product was extracted into ethyl acetate
  3. washthe combined extracts were washed once with 1M K2CO3 and once with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0c9dd5689ed7488a98945cc14a4e58c1
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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