Pyridine → HCID 7938037, compound

HRID 516805Notes

Reaction equation

HRID 516805 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-4545609a7d534a67a368e56b32da41ae
Source dataset
uspto-grants-2015_08
Patent number
US09115064B2

Reaction notes

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