1,1'-Thiocarbonyldiimidazole → HCID 51003043, compound

HRID 929659Notes

Reaction equation

HRID 929659 reaction equation
C1N=C[N:3]([C:6]([N:8]2[CH:12]=[N:11][CH:10]=[CH:9]2)=[S:7])C=1.C1C2[C:17](=[CH:18][CH:19]=[CH:20]C=2)[CH:16]=[C:15](N)N=1.C([O-])(=O)C.[NH4+]>C(#N)C>[CH:10]1[C:9]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:12]([NH:8][C:6]([NH2:3])=[S:7])[N:11]=1

Participants

5

Reactant 3

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 311869Isoquinolin-3-AmineHCID 517165Ammonium Acetate

Product 1

HCID 51003043HCID 51003043, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

0.618 g (3.47 mmol) N,N′-thiocarbonyldiimidazole was dissolved in 20 mL acetonitrile, and 0.500 g (3.47 mmol) isoquinoline-3-amine in the form of a suspension in 15 mL acetonitrile was added dropwise in portions. The clear orange solution which formed was stirred for 12 hr, whereupon a reddish precipitate formed. The intermediate product was directly reacted, without workup, with 0.535 g (6.940 mmol) ammonium acetate for 25 min at 85° C. in a CEM microwave (100 watts). The solvent was removed under vacuum. The residue was stirred in water, and the resulting precipitate was suctioned off and washed with water. For further purification the solid was taken up in 5 mL acetonitrile and combined with 50 mL diisopropyl ether. The precipitate was filtered again and dried in a vacuum drying oven at 40° C., resulting in the isolation of 0.540 g (2.647 mmol, 76%) purified N-isoquinolin-3-yl-thiourea.

Workup

  1. customThe clear orange solution which formed
  2. customformed
  3. customThe solvent was removed under vacuum
  4. stirringThe residue was stirred in water
  5. washwashed with water
  6. customFor further purification the solid
  7. filtrationThe precipitate was filtered again
  8. customdried in a vacuum
  9. customdrying oven at 40° C.
  10. customresulting in the isolation of 0.540 g (2.647 mmol, 76%)
  11. custompurified N-isoquinolin-3-yl-thiourea

Sources & evidence

ORD record
ord-b7227b64f986475fb136136bbea98951
Source dataset
uspto-grants-2016_03
Patent number
US09296697B2

Reaction notes

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