Thiophosgene → HCID 19005818, compound

HRID 1742803Notes

Reaction equation

HRID 1742803 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([C:16]1[NH:17][C:18](=[O:25])[C:19]([CH:22]([CH3:24])[CH3:23])([CH3:21])[N:20]=1)[C:10]([C:26]([OH:28])=[O:27])=[CH:9]2>CO>[CH:22]([C:19]1([CH3:21])[C:18](=[O:25])[NH:17][C:16]([C:11]2[C:10]([C:26]([OH:28])=[O:27])=[CH:9][C:8]3[C:13](=[CH:14][CH:15]=[C:6]([N:5]=[C:1]=[S:2])[CH:7]=3)[N:12]=2)=[N:20]1)([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 19005819HCID 19005819, compound

Product 1

HCID 19005818HCID 19005818, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thiophosgene (0.12 mL, 1.56 mmol) is added to a solution of the above prepared formula III 6-amino-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid (170 mg, 0.521 mmol) and methanol (25 mL). The reaction mixture is stirred for five minutes at room temperature and then concentrated in vacuo. The residue is redissolved into a small amount of methanol, filtered and the filtrate is added to 25 mL of ether. The resulting precipitate is collected, washed with ether and dried under reduced pressure to give 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) -6-isothiocyano-3-quinolinecarboxylic acid as a brown powder (190 mg). The product is obtained in the form of a tricyclic anhydride which hydrolyses to the acid in water or during subsequent reaction in aqueous media. The purity of this material is determined by TLC on silica gel with chloroform, methanol and acetic acid (220:30:6) elution.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is redissolved into a small amount of methanol
  3. filtrationfiltered
  4. additionthe filtrate is added to 25 mL of ether
  5. customThe resulting precipitate is collected
  6. washwashed with ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-93d6b9ff1f5d46fcad34d7cdf2e027f6
Source dataset
uspto-grants-1994_08
Patent number
US05342771

Reaction notes

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