Pyridine → HCID 86665540, compound

HRID 1770749Notes

Reaction equation

HRID 1770749 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][C:7]([CH3:10])([CH3:9])[NH:6][C:5]1=[O:11].N1C=CC=CC=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>ClCCl>[CH3:18][S:19]([O:1][CH2:2][CH2:3][N:4]1[CH2:8][C:7]([CH3:9])([CH3:10])[NH:6][C:5]1=[O:11])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 67509984HCID 67509984, compound

Product 1

HCID 86665540HCID 86665540, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(2-hydroxyethyl)-4,4-dimethylimidazolidin-2-one (5.9 g, 37 mmol) and pyridine (3.6 mL, 44.4 mmol) in 150 mL of anhydrous dichloromethane was added methanesulfonyl chloride (3.3 mL, 43 mmol). The reaction was stirred at room temperature for 20 hours, then diluted with 100 mL of dichlormethane and washed twice with 40 mL of 1 N HCl and once with brine. The organic fraction was dried over sodium sulfate and concentrated in vacuo to 3.54 g of the desired product as white solid. 1H NMR (CDCl3, 400 MHz) δ 1.33 (s, 6H), 3.06 (s, 3H), 3.23 (s, 2H), 3.54-3.57 (t, J=5.2, 2H), 4.36-4.39 (t, J=5.2 Hz, 2H); LRMS (ESI/APCI) m/z 237 [M+H]+.

Workup

  1. washwashed twice with 40 mL of 1 N HCl and once with brine
  2. dry with materialThe organic fraction was dried over sodium sulfate
  3. concentrationconcentrated in vacuo to 3.54 g of the desired product as white solid

Sources & evidence

ORD record
ord-3a703f89dbc74e0db58f9c7a5f7eb60f
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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