Hydrazine → HCID 178434382, compound

HRID 706776Notes

Reaction equation

HRID 706776 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][C:7]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=3[Cl:28])(=[O:20])=[O:19])=[CH:13][CH:12]=2)=[N:8][C:9]=1Cl)(=O)[CH3:2].[NH2:29][NH2:30]>CC(O)C.O>[Cl:28][C:22]1[C:23]([Cl:27])=[CH:24][CH:25]=[CH:26][C:21]=1[S:18]([NH:17][C:14]1[CH:15]=[CH:16][C:11]([C:7]2[N:8]=[C:9]3[NH:29][N:30]=[C:1]([CH3:2])[C:4]3=[N:5][CH:6]=2)=[CH:12][CH:13]=1)(=[O:20])=[O:19]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 86678949N-[4-(5-acetyl-6-chloro-pyrazin-2-yl)-phenyl]-2,3-dichloro-benzenesulfonamide

Product 1

HCID 178434382HCID 178434382, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

N-[4-(5-acetyl-6-chloro-pyrazin-2-yl)-phenyl]-2,3-dichloro-benzenesulfonamide (230 mg) was suspended in a mixture of 2 ml iPrOH and 2 ml 35% hydrazine in water at RT and heated to 120° C. by microwave irradiation (Biotage Initiator™ apparatus) for 20 min under stirring in a sealed vessel. The reaction mixture was left to cool to RT, quenched with a saturated aqueous sodium bicarbonate solution (10 ml) and extracted with EtOAc (3×30 ml). The combined organic phases were dried over sodium sulfate, filtered and evaporated to afford the crude product. Purification by recrystallisation from an acetone-water mixture afforded the title compound as a pale yellow solid after drying under vacuum. Yield: 81.6 mg (38%).

Workup

  1. waitThe reaction mixture was left
  2. temperatureto cool to RT
  3. customquenched with a saturated aqueous sodium bicarbonate solution (10 ml)
  4. extractionextracted with EtOAc (3×30 ml)
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford the crude product
  9. customPurification
  10. customby recrystallisation from an acetone-water mixture

Sources & evidence

ORD record
ord-8d2b471f888443baa4e50695afcf7393
Source dataset
uspto-grants-2015_11
Patent number
US09174993B2

Reaction notes

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