Diethyl Ether → HCID 4135863, compound

HRID 392451Notes

Reaction equation

HRID 392451 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.[CH2:9]([S:11](Cl)(=[O:13])=[O:12])[CH3:10].C(OCC)C>ClCCl>[CH2:9]([S:11]([NH:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)(=[O:13])=[O:12])[CH3:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11667Ethanesulfonyl chlorideHCID 310183-Pyridinemethanamine

Product 1

HCID 4135863HCID 4135863, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Aminomethylpyridine (2.15 g, 19.88 mmol) was dissolved in 40 ml dichloromethane. Ethanesulfonyl chloride (2.56 g, 19.9 mmol) was added to the mixture and stirred for 18 h. To the resultant precipitate was added 40 ml diethyl ether and decanted from the solid. The solid was partitioned between a mixture of 100 ml dichloromethane/20 ml isopropyl alcohol and 20 ml of a saturated sodium bicarbonate solution. The organic layer was separated and the aqueous phase extracted twice with the 80/20 mixture of dichloromethane/isopropyl alcohol. The organic layers were combined, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound. 1H NMR: 8.67 (s,1H), 8.60 (d,1H,J=4 Hz), 7.90 (m,1H), 7.42 (m,1H), 5.77 (t,1H,J=6 Hz), 4.38 (d,2H,J=6 Hz), 3.07 (t,2H,J=8 Hz), 1.38 (t,3H,J=8 Hz). MS calcd. 200.2; MS (M+1) 201.1.

Workup

  1. customdecanted from the solid
  2. customThe solid was partitioned between a mixture of 100 ml dichloromethane/20 ml isopropyl alcohol and 20 ml of a saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. extractionthe aqueous phase extracted twice with the 80/20 mixture of dichloromethane/isopropyl alcohol
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-37c967361f1d428faa696815f107b502
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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