Iodine chloride → Benzenamine, 4-(2-benzothiazolyl)-2-iodo-

HRID 1636552

Reaction equation

HRID 1636552 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[I:17]Cl>C(O)(=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][C:7]=1[I:17]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 2344752-(4-Aminophenyl)benzothiazole

Product 1

HCID 384526Benzenamine, 4-(2-benzothiazolyl)-2-iodo-Yield 71.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution in acetic acid (35 ml) of 2-(4'-aminophenyl) benzothiazole (2.98 g, 0.0132 mol) prepared as above was added dropwise a solution of iodine monochloride (2.78 g, 0.0171 mol) in acetic acid (35 ml) over 10 minutes at room temperature, followed by stirring for 11/2 hours. After evaporation of the solvent, 60 ml dichloromethane was added to the residue and the resulting suspension was neutralised with sodium hydrogen carbonate. Then 300 ml of water was added. The organic layer was washed with 10% sodium hydrogen carbonate solution (150 ml), water (100 ml×2) and dried (mgSO4). The solvent was removed under reduced pressure, absorbed onto silica gel, and placed on top of a column of silica gel. Flash elution using ethyl acetate-hexane (2:5) yielded brown crystals (3.32 g, 69.6%), m.p. 143-144° C.

Workup

  1. customAfter evaporation of the solvent, 60 ml dichloromethane
  2. additionwas added to the residue
  3. additionThen 300 ml of water was added
  4. washThe organic layer was washed with 10% sodium hydrogen carbonate solution (150 ml), water (100 ml×2)
  5. customdried (mgSO4)
  6. customThe solvent was removed under reduced pressure
  7. customabsorbed onto silica gel
  8. washFlash elution

Sources & evidence

ORD record
ord-74a90100369d4fcf8789b0b766258894
Source dataset
uspto-grants-2000_03
Patent number
US06034246

Linked notes

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