Pyridine → HCID 7938037, compound

HRID 1516968Notes

Reaction equation

HRID 1516968 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-0b271b381f2f4d939757dba62c21c9d6
Source dataset
uspto-grants-2012_07
Patent number
US08227639B2

Reaction notes

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