Pyridine → HCID 7938037, compound

HRID 1189718Notes

Reaction equation

HRID 1189718 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].N1C=CC=CC=1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.S(Cl)(Cl)(=O)=O>C(Cl)Cl>[N:18]1([S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])(=[O:10])=[O:9])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8083MorpholineHCID 24648Sulfuryl chlorideHCID 761872-Chlorobenzenesulfonyl chloride

Product 1

HCID 7938037HCID 7938037, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of a 2-chlorobenzene sulfonyl chloride (10 g, 47.4 mmol) in DCM (100 ml) cooled to 0° C. was added pyridine (5.7 ml, 71.1 mmol) and morpholine (6.2 ml, 71.1 mmol) dropwise. Stirring was continued for 15 minutes after which time no sulfonyl chloride was evident by LC-MS. The reaction was quenched by the addition of 2N HCl, washed with further portions of 2N HCl, dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound without need for additional purification. (11.2 g, 100%). δH (400 MHz, DMSO-d6) 7.97 (1H, dd, 7.8, 1.5 Hz), 7.66-7.77 (2H, m), 7.58 (1H, ddd, 8.1, 6.7, 1.8 Hz), 3.57-3.64 (4H, m), 3.11-3.18 (4H, m); TR=1.25 min.

Workup

  1. customThe reaction was quenched by the addition of 2N HCl
  2. washwashed with further portions of 2N HCl
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75d44b1e18d14fea963e1b5eaac7c73e
Source dataset
uspto-grants-2014_03
Patent number
US08674132B2

Reaction notes

Loading…