Ethanesulfonylchloride, 2-chloro- → HCID 66748912, compound

HRID 1748105Notes

Reaction equation

HRID 1748105 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-ddd6fae7b55f4c12a5d757622299031f
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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