Sodium Cyanate → HCID 13505960, compound

HRID 1981531Notes

Reaction equation

HRID 1981531 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[O-:13][C:14]#[N:15].[Na+]>C(O)(=O)C.O>[NH:1]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2)[C:14]([NH2:15])=[O:13]

Participants

5

Reactant 2

HCID 517096Sodium CyanateHCID 49127596-amino-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 13505960HCID 13505960, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

6-Amino-3,4-dihydrocarbostyril (1.6 g) is dissolved in a mixture of acetic acid (5 ml) and water (10 ml), and thereto is added dropwise a solution of sodium cyanate (1.3 g) in water (9 ml) with stirring at room temperature. The mixture is stirred at the same temperature for 1 hour. After the reaction, the resulting precipitate is separated by filtration, washed with water, purified by silica gel column chromatography (solvent; chloroform:methanol=50:1), and recrystallized from dimethylformamide-water to give 6-ureido-3,4-dihydrocarbostyril (0.45 g) as colorless needles, m.p.>300° C.

Workup

  1. stirringThe mixture is stirred at the same temperature for 1 hour
  2. customAfter the reaction
  3. customthe resulting precipitate is separated by filtration
  4. washwashed with water
  5. custompurified by silica gel column chromatography (solvent; chloroform:methanol=50:1)
  6. customrecrystallized from dimethylformamide-water

Sources & evidence

ORD record
ord-53ef395903d44e4fbe3fca83ad08d7b2
Source dataset
uspto-grants-1986_06
Patent number
US04593035

Reaction notes

Loading…