Ethanesulfonylchloride, 2-chloro- → HCID 56655832, compound

HRID 2035856Notes

Reaction equation

HRID 2035856 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[CH3:10][C:11]1[CH:30]=[CH:29][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:23]([NH2:28])=[N:24][CH:25]=[CH:26][CH:27]=3)=[CH:18][CH:17]=2)=[CH:13][CH:12]=1>C1COCC1>[CH3:10][C:11]1[CH:12]=[CH:13][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:23]4=[N:28][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:24]4[CH:25]=[CH:26][CH:27]=3)=[CH:18][CH:17]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 667477452-Pyridinamine, 3-[4-(4-methylphenoxy)phenyl]-

Product 1

HCID 56655832HCID 56655832, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (60%, 1.57 g) in THF (dry) (60 ml) was added 2-chloroethanesulfonyl chloride (1.652 mL) at 0° C. and the mixture was stirred for 10 min at the same temperature. A solution of 3-(4-(4-methylphenoxy)phenyl)pyridin-2-amine (2.17 g) in THF (dry) (40 mL) was added at 0° C. and the mixture was stirred at room temperature under nitrogen overnight. The mixture was quenched with water at 0° C. Water, EtOAc and IPE were added and the precipitates were collected, washed with water/EtOAc, and dried in vacuo. The precipitates were crystallized from DMSO (15 mL)/EtOH (200 ml) at 80° C. to room temperature to give the title compound (1.91 g) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature under nitrogen overnight
  2. customThe mixture was quenched with water at 0° C
  3. additionWater, EtOAc and IPE were added
  4. customthe precipitates were collected
  5. washwashed with water/EtOAc
  6. customdried in vacuo
  7. customThe precipitates were crystallized from DMSO (15 mL)/EtOH (200 ml) at 80° C. to room temperature

Sources & evidence

ORD record
ord-2c75763ab0744a67be4c1f28797d8f04
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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