Benzoyl isothiocyanate → HCID 9886701, compound
Reaction equation
C([N:9]=[C:10]=[S:11])(=O)C1C=CC=CC=1.[CH:12]1[C:13]2[C:28](=[O:29])[C:27]([C:30]([OH:32])=[O:31])=[CH:26][N:25]([CH:33]3[CH2:35][CH2:34]3)[C:14]=2[CH:15]=[C:16]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:17]=1[F:18].[Na]>C1COCC1>[NH2:9][C:10](=[S:11])[N:22]1[CH2:21][CH2:20][N:19]([C:16]2[CH:15]=[C:14]3[C:13]([C:28](=[O:29])[C:27]([C:30]([OH:32])=[O:31])=[CH:26][N:25]3[CH:33]3[CH2:34][CH2:35]3)=[CH:12][C:17]=2[F:18])[CH2:24][CH2:23]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 41 fahrenheit
Procedure
[6R-[6a,7b]]-3-[[[(3-Carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-4-piperazinyl]iminomethyl]thio methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo [4.2.0]oct-2-ene-2-carboxylic acid sodium salt, of the following formula ##STR331## according to this invention, is made as follows. A solution of benzoyl isothiocyanate (0.92 g) in THF (20 ml) is added to a mixture of ciprofloxacin sodium salt (2.0 g) in THF (300 ml), and the reaction is stirred for 20 hours. The reaction is concentrated to dryness and the residue is triturated with acetone. The resultant benzoylurea is added to a preheated at approximately 80° C. (176° F.) solution of 5% aqueous NaOH and the reaction is stirred for 30 minutes. The mixture is cooled to approximately 5° C. (41° F.) and acidified with 1N HCl. The solid is collected by filtration and recrystallized from DMF to yield 7-[4-(aminothioxomethyl)-1-piperazinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.