Hydrochloric Acid → HCID 21506583, compound

HRID 1287824Notes

Reaction equation

HRID 1287824 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH2:12])[CH:5]=[CH:4][CH:3]=1.[OH:13][C:14]([CH3:20])([CH2:18][CH3:19])[C:15](O)=O.C(O)C.CCOCC.[ClH:29]>>[ClH:29].[CH2:18]([C:14]([CH3:20])([C:15]1[NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[C:10]([N:12]=1)=[CH:9][CH:8]=[CH:7]3)[OH:13])[CH3:19]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3283Diethyl EtherHCID 680671,8-DiaminonaphthaleneHCID 95433(+-)-2-Hydroxy-2-methylbutyric acid

Product 1

HCID 21506583HCID 21506583, compound

Procedure

1,8-Diaminonaphthalene (44.5 g, 0.282 mole) is suspended in 400 ml of 4N hydrochloric acid. To this suspension is added 2-hydroxy-2-methyl butyric acid (50 g, 0.423 mole) and the whole is stirred and heated under reflux for 96 hours. Then the reaction mixture is allowed to cool and is filtered, yielding a gray-green solid. The solid is heated and stirred with 1 liter of refluxing ethanol, and is filtered while hot to remove unreacted starting materials. The filtrate is concentrated to dryness and the resulting solid is treated with 500 ml of boiling ethanol. After the insoluble material is removed by filtration, the filtrate was treated with charcoal, yielding a yellow solution. Addition of ether, plus cooling, yields a yellow-brown solid. Recrystallization from ethanol (charcoal) yields the desired product, α-ethyl-α-methyl-2-perimidinemethanol, hydrochloride, m.p. 266°-268° dec.).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 96 hours
  3. temperatureto cool
  4. filtrationis filtered
  5. customyielding a gray-green solid
  6. temperatureThe solid is heated
  7. filtrationis filtered while hot
  8. customto remove unreacted
  9. concentrationThe filtrate is concentrated to dryness
  10. additionthe resulting solid is treated with 500 ml of boiling ethanol
  11. customAfter the insoluble material is removed by filtration
  12. additionthe filtrate was treated with charcoal
  13. customyielding a yellow solution
  14. temperaturecooling
  15. customyields a yellow-brown solid
  16. customRecrystallization from ethanol (charcoal)

Sources & evidence

ORD record
ord-e1af9030031c4f1e88d710bd1304b678
Source dataset
uspto-grants-1976_10
Patent number
US03985880

Reaction notes

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