Diisopropyl Ether → HCID 19431474, compound

HRID 1077430Notes

Reaction equation

HRID 1077430 reaction equation
C(N(CC)CC)C.[NH2:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]3[CH:19]=[CH:20][C:21](=[O:24])[NH:22][N:23]=3)[CH:15]=2)[CH2:10]1.Br.[CH2:26]([N:29]=[C:30]=[S:31])[CH2:27][CH3:28].C(OC(C)C)(C)C>COCCO.O>[CH2:26]([NH:29][C:30]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]3[CH:19]=[CH:20][C:21](=[O:24])[NH:22][N:23]=3)[CH:15]=2)[CH2:10]1)=[S:31])[CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 8471TriethylamineHCID 69403Propyl IsothiocyanateHCID 189297722-amino-5-[pyridazin-3(2H)-on-6-yl]indane hydrobromide

Product 1

HCID 19431474HCID 19431474, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Procedure

Triethylamine (2.0 g) was added to 60 ml of a suspension containing 5.04 g of 2-amino-5-[pyridazin-3(2H)-on-6yl]indane·hydrobromide suspended in 2-methoxyethanol, and the mixture was stirred for 10 minutes. Then, 2.33 g of propyl isothiocyanate was added dropwise to the mixture, and the resulting mixture was stirred at 50° C. for 7 hours. After cooling, 100 ml of water and 300 ml of isopropyl ether were added to the reaction mixture, and the resulting mixture was stirred. Crystals precipitated were collected by filtration, washed with water and dried. The crystals obtained were recrystallized from ethanol to obtain 4.53 g of 2-[(propyl)thiocarbamoyl]amino-5-[pyridazin-3(2H)-on-6yl]indane.

Workup

  1. stirringthe resulting mixture was stirred at 50° C. for 7 hours
  2. temperatureAfter cooling
  3. stirringthe resulting mixture was stirred
  4. customCrystals precipitated
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried
  8. customThe crystals obtained
  9. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-e555787896b2482faaa96a5f1388201d
Source dataset
uspto-grants-1996_08
Patent number
US05543409

Reaction notes

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