Benzoyl isothiocyanate → HCID 9886701, compound

HRID 265249Notes

Reaction equation

HRID 265249 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]1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 6723330993107-09-6

Product 1

HCID 9886701HCID 9886701, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
41 fahrenheit

Procedure

[6R-[6a,7b]]-3-[[[(3-Carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1-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 ##STR330## according to this invention, is made as follows. A solution of benzoyl isothiocyanate 10.92 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.

Workup

  1. concentrationThe reaction is concentrated to dryness
  2. customthe residue is triturated with acetone
  3. additionThe resultant benzoylurea is added to
  4. customa preheated at approximately 80° C.
  5. custom(176° F.) solution of 5% aqueous NaOH
  6. stirringthe reaction is stirred for 30 minutes
  7. filtrationThe solid is collected by filtration
  8. customrecrystallized from DMF

Sources & evidence

ORD record
ord-25c4c72ec3424d0f858a18fcde2bf6f1
Source dataset
uspto-grants-1997_07
Patent number
US05648346

Reaction notes

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