Sodium Hydroxide → HCID 20266541, compound

HRID 1719695Notes

Reaction equation

HRID 1719695 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH2:9])[CH:5]=[N:4][CH:3]=[N:2]1.[OH-].[Na+].[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](Cl)=[O:18]>C(Cl)Cl>[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:17]([C:13]2[O:12][CH:16]=[CH:15][CH:14]=2)=[O:18])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 682422-Furancarbonyl chlorideHCID 43796821H-1,2,4-Triazole-1-propanamine

Product 1

HCID 20266541HCID 20266541, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of about 3.78 g of 1H-1,2,4-triazole-1-propanamine, about 33 ml of 1N sodium hydroxide and about 100 ml of methylene chloride was stirred, then about 3.3 ml of 2-furoyl chloride was added. The mixture was stirred overnight, then about 15 ml of 1N sodium hydroxide and about 100 ml of methylene chloride were added. The mixture was shaken, the organic layer separated, washed with two approximately 50 ml portions of water, dried, filtered and evaporated to an oil. Ether was added to the oil which was then triturated and the crystals collected. These were recrystallized from ether giving about 2.0 g of the desired product as beige crystals, mp 63°-66° C. The fumarate salt melts at 65° C.-70° C.

Workup

  1. stirringThe mixture was stirred overnight
  2. stirringThe mixture was shaken
  3. customthe organic layer separated
  4. washwashed with two approximately 50 ml portions of water
  5. customdried
  6. filtrationfiltered
  7. customevaporated to an oil
  8. additionEther was added to the oil which
  9. customwas then triturated
  10. customthe crystals collected
  11. customThese were recrystallized from ether giving about 2.0 g of the desired product as beige crystals, mp 63°-66° C

Sources & evidence

ORD record
ord-7ebaf73f1b474ab488767cb5a0a02719
Source dataset
uspto-grants-1985_09
Patent number
US04542145

Reaction notes

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