Ethanesulfonylchloride, 2-chloro- → HCID 66748912, compound

HRID 2035993Notes

Reaction equation

HRID 2035993 reaction equation
Cl[CH2:2][CH2:3][S:4](Cl)(=[O:6])=[O:5].[H-].[Na+].[CH:10](/[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25]([NH2:30])=[N:26][CH:27]=[CH:28][CH:29]=2)=[CH:20][CH:19]=1)=[CH:11]\[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[C:12]1(/[CH:11]=[CH:10]/[C:18]2[CH:23]=[CH:22][C:21]([C:24]3[C:25]4=[N:30][S:4](=[O:6])(=[O:5])[CH2:3][CH2:2][N:26]4[CH:27]=[CH:28][CH:29]=3)=[CH:20][CH:19]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 66748647HCID 66748647, compound

Product 1

HCID 66748912HCID 66748912, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Chloroethanesulfonyl chloride (0.410 mL) was added to a mixture of NaH (60%, 390 mg) in THF (dry) (8 mL) at 0° C. under nitrogen flow. The mixture was stirred at 0° C. for 5 min. The mixture of (E)-3-(4-styrylphenyl)pyridin-2-amine (531 mg) in THF (dry) (20 mL) was added dropwise and the mixture was stirred at room temperature under atmosphere overnight. The mixture was quenched with water at 0° C., and water, EtOAc and THF were added. The insoluble material was collected by filtration and crystallized from DMSO-EtOH to give the title compound (340 mg) as slightly pale yellow crystals.

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred at room temperature under atmosphere overnight
  3. customThe mixture was quenched with water at 0° C.
  4. additionwater, EtOAc and THF were added
  5. filtrationThe insoluble material was collected by filtration
  6. customcrystallized from DMSO-EtOH

Sources & evidence

ORD record
ord-5fe83f8f133b4ca3bcc044d1b6cd609a
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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