Dehydrothio-4-toluidine → HCID 391871, compound

HRID 1636553Notes

Reaction equation

HRID 1636553 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]([CH3:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[I:18]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]([CH3:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][C:7]=1[I:18]

Participants

4

Reactant 2

HCID 7087Dehydrothio-4-toluidineHCID 24640Iodine chloride

Product 1

HCID 391871HCID 391871, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(4'-Aminophenyl)-6-methylbenzothiazole (0.6 g, 2.5 mmol) was treated with iodine monochloride (0.5 g, 3.02 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 (0.61 g, 66.7%), m.p. 176.2-177.9° C.

Workup

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

Sources & evidence

ORD record
ord-442f96b0a9c44ac48f43768ccb110f5c
Source dataset
uspto-grants-2000_03
Patent number
US06034246

Reaction notes

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