Hydrochloric Acid → HCID 20436796, compound

HRID 1395583Notes

Reaction equation

HRID 1395583 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:9][CH2:10][NH:11][CH:12]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:13]([O:15]CC)=O.[O-:34][C:35]#[N:36].[K+].Cl>C(O)C.O>[CH2:27]([O:26][C:24]([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH:12]1[N:11]([CH2:10][CH2:9][CH:8]([O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:35](=[O:34])[NH:36][C:13]1=[O:15])=[O:25])[CH3:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11378442Potassium cyanateHCID 20436821HCID 20436821, compound

Product 1

HCID 20436796HCID 20436796, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of diethyl 2-(3-(tetrahydropyran-2-yloxy)octylamino)nonanedioate (7.8 g) in ethanol (32 ml) was added a solution of potassium cyanate (3.0 g) in water (6 ml). The resulting suspension was stirred and cooled during the gradual addition of 2 N-hydrochloric acid (16.7 ml). The solution was allowed to stand at room temperature for 22 hours, most of the ethanol was evaporated, water was added, and the insoluble oil was extracted with ether. The ether solution was washed with water, dried over magnesium sulphate, and evaporated. The yellow oil so obtained (8.0 g) was dissolved in light petroleum (b.p. 60°-80° C.) and the solution was refluxed for 4 hours, evaporated to dryness, and the residual oil was heated on the steambath for 2 hours to give 5-(6-ethoxycarbonylhexyl)-1-(3-(tetrahydropyran-2-yloxy)octyl)hydantoin as a yellow oil (7.3 g), which was used without further purification.

Workup

  1. customwas evaporated
  2. additionwater was added
  3. extractionthe insoluble oil was extracted with ether
  4. washThe ether solution was washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe yellow oil so obtained (8.0 g)
  8. temperaturethe solution was refluxed for 4 hours
  9. customevaporated to dryness
  10. temperaturethe residual oil was heated on the steambath for 2 hours

Sources & evidence

ORD record
ord-f5cc8880e4484ce6884511e51701904d
Source dataset
uspto-grants-1980_05
Patent number
US04204068

Reaction notes

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