Iodine chloride → 2-(4'-Amino-3'-iodophenyl)-6-methoxybenzothiazole

HRID 1636554Notes

Reaction equation

HRID 1636554 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[I:19]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]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][C:7]=1[I:19]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)aniline

Product 1

HCID 100684372-(4'-Amino-3'-iodophenyl)-6-methoxybenzothiazoleYield 56.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(4'-Aminophenyl)-6-methoxybenzothiazole (0.22 g, 0.84 mmol) was treated with iodine monochloride (0.21 g, 1.3 mmol) in acetic acid according to the above-described general procedure for iodination. Crude product was purified by flash chromatography on silica gel, using ethyl acetate-hexane (1:3) as eluent, to give brown small crystals (0.18 g, 54.9%), m.p. 179.2-181.1° C.

Workup

  1. customCrude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-06fc31bab1024d1a891d176b03be7e52
Source dataset
uspto-grants-2000_03
Patent number
US06034246

Reaction notes

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