Water → HCID 66747936, compound

HRID 1748095Notes

Reaction equation

HRID 1748095 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15]([NH2:20])=[N:16][CH:17]=[CH:18][N:19]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:24][CH2:25][S:26](Cl)(=[O:28])=[O:27].O>C1COCC1.CCOC(C)=O>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[C:15]3=[N:20][S:26](=[O:28])(=[O:27])[CH2:25][CH2:24][N:16]3[CH:17]=[CH:18][N:19]=2)=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 66748419HCID 66748419, compound

Product 1

HCID 66747936HCID 66747936, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(4-phenoxyphenyl)pyrazin-2-amine (1.97 g) in THF (dry) (20 mL) was added to a suspension of NaH (60%, 1.50 g) and 2-chloroethanesulfonyl chloride (2.35 mL) in THF (dry) (20 mL) at 0° C. The mixture was stirred at room temperature overnight then at 80° C. for 4 hr. After cooling to room temperature, the mixture was added with water and EtOAc. The precipitate was collected by filtration, washed with water and EtOAc, and then recrystallized from EtOH-EtOAc to give the title compound (1.68 g) as a pale yellow solid.

Workup

  1. waitat 80° C. for 4 hr
  2. temperatureAfter cooling to room temperature
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water and EtOAc
  5. customrecrystallized from EtOH-EtOAc

Sources & evidence

ORD record
ord-5cec624a010b4a03a16a9a7975c68d41
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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