Iodine → HCID 19890703, compound

HRID 893581Notes

Reaction equation

HRID 893581 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:16]=[C:15]3[C:10]([C:11](=[O:23])[C:12]([C:20]([OH:22])=[O:21])=[C:13]4[S:18][CH:17]([CH3:19])[N:14]43)=[CH:9][C:8]=2[F:24])[CH2:3]1.II.[Cl:27]S(O)(=O)=O>>[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]([Cl:27])=[C:15]3[C:10]([C:11](=[O:23])[C:12]([C:20]([OH:22])=[O:21])=[C:13]4[S:18][CH:17]([CH3:19])[N:14]43)=[CH:9][C:8]=2[F:24])[CH2:3]1

Participants

4

Reactant 3

HCID 807IodineHCID 24638Chlorosulfonic acidHCID 14421101HCID 14421101, compound

Product 1

HCID 19890703HCID 19890703, compound

Procedure

To a solution of 1.80 g of 7-(3-amino-1-pyrrolidinyl)-6-fluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid in 10 ml of chlorosulfonic acid, a trace of iodine was added, and the mixture was bubbled with chlorine gas for 3.5 hours under ice-cooling with stirring. The reaction mixture was poured into ice-water and neutralized to pH 8 with 10% aqueous sodium hydroxide. The precipitate obtained was collected by filtration and converted to the methanesulfonate. The salt was dissolved into water and filtered. The filtrate was neutralized to pH 8 with 10% aqueous sodium hydroxide. The precipitate was collected by filtration to give 1.50 g of pale yellowish-brown crystals.

Workup

  1. customthe mixture was bubbled with chlorine gas for 3.5 hours under ice-
  2. temperaturecooling
  3. additionThe reaction mixture was poured into ice-water and neutralized to pH 8 with 10% aqueous sodium hydroxide
  4. customThe precipitate obtained
  5. filtrationwas collected by filtration
  6. dissolutionThe salt was dissolved into water
  7. filtrationfiltered
  8. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-884515b2e17f4dcda7f775d9df4a61c8
Source dataset
uspto-grants-1992_06
Patent number
US05126337

Reaction notes

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