Iodine chloride → 4-Fluoro-2-(4'-amino-3'-iodophenyl)benzothiazole

HRID 25264

Reaction equation

HRID 25264 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[I:18]Cl>C(O)(=O)C>[F:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([I:18])[CH:12]=3)[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 101987334-(4-Fluoro-benzothiazol-2-yl)-phenylamine

Product 1

HCID 99073854-Fluoro-2-(4'-amino-3'-iodophenyl)benzothiazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of the 4-fluoro-2-(4′-aminophenyl)benzothiazole prepared as described in Example 3 (4.5 mmol) in acetic acid (20 ml) was added dropwise to a solution of iodine monochloride (5.8 mmol) in acetic acid (20 ml) at 25° C. The resulting solution was stirred for 2 hr, then the solvent was removed under vacuum. The residue was dissolved in chloroform (100 ml) and washed with aqueous sodium carbonate (50 ml), aqueous sodium thiosulfate (50 ml) and water (50 ml). Evaporation of the solvent, followed by column chromatography (chloroform) and recrystallization from methanol gave pale cream needles.

Workup

  1. customthe solvent was removed under vacuum
  2. dissolutionThe residue was dissolved in chloroform (100 ml)
  3. washwashed with aqueous sodium carbonate (50 ml), aqueous sodium thiosulfate (50 ml) and water (50 ml)
  4. customEvaporation of the solvent
  5. customfollowed by column chromatography (chloroform) and recrystallization from methanol
  6. customgave pale cream needles

Sources & evidence

ORD record
ord-bbf5a827234a40c89a9494fb927ae3dd
Source dataset
uspto-grants-2005_02
Patent number
US06858633B1

Linked notes

Loading…