2-Aminoquinoline → HCID 20246879, compound

HRID 929660Notes

Reaction equation

HRID 929660 reaction equation
C1N=C[N:3]([C:6](N2C=NC=C2)=[S:7])C=1.[NH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.C([O-])(=O)C.[NH4+]>C(#N)C.CO>[N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[NH:13][C:6]([NH2:3])=[S:7]

Participants

6

Reactant 3

HCID 113792-AminoquinolineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 517165Ammonium Acetate

Product 1

HCID 20246879HCID 20246879, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent2×

Procedure

1.496 g (8.394 mmol) N,N′-thiocarbonyldiimidazole was dissolved in 30 mL acetonitrile, and 1.210 g (8.394 mmol) 2-amino-quinoline dissolved in 15 mL acetonitrile was added dropwise at room temperature. After 1 hr a precipitate deposited, and stirring was performed for an additional 12 hr. The solid was filtered off, and without further purification was reacted directly with 1.294 g (16.789 mmol) ammonium acetate in 50 mL methanol for 5 hr at 40° C. After mass spectrometric analysis the solvent was removed under vacuum, and the batch was dissolved in dichloromethane and shaken out with water (1×50 mL). The organic phase was dried over magnesium sulfate and filtered, and the solvent was removed under vacuum. The crude product was purified by column chromatography on silica gel (column Ø=3 cm, h=15 cm), first with dichloromethane as eluent, then with methanol to increase the polarity, and finally with pure methanol. The clean fraction was purified and the solvent was removed under vacuum, resulting in a total of 0.70 g (3.445 mmol, 41%) N-quinolin-2-yl-thiourea.

Workup

  1. additionwas added dropwise at room temperature
  2. waitwas performed for an additional 12 hr
  3. filtrationThe solid was filtered off
  4. customwithout further purification
  5. customAfter mass spectrometric analysis the solvent was removed under vacuum
  6. dissolutionthe batch was dissolved in dichloromethane
  7. stirringshaken out with water (1×50 mL)
  8. dry with materialThe organic phase was dried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent was removed under vacuum
  11. customThe crude product was purified by column chromatography on silica gel (column Ø=3 cm, h=15 cm), first with dichloromethane as eluent
  12. temperaturewith methanol to increase the polarity
  13. customThe clean fraction was purified
  14. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-24ecc1533c1f48869c464ab77854732a
Source dataset
uspto-grants-2016_03
Patent number
US09296697B2

Reaction notes

Loading…