Sodium Iodide → Iodophenylhydrazine

HRID 1459131Notes

Reaction equation

[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCC[Sn](CCCC)CCCC.CCCC[Sn](CCCC)CCCC.[I-:35].[Na+].CC1C=CC(S(NCl)(=O)=O)=CC=1>>[I:35][N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[NH2:8]

Participants

Reactant 4

HCID 5238Sodium Iodide

HCID 7516Phenylhydrazine2×

HCID 31388Tosylchloramide

HCID 6327815Hexabutyldistannane

Product 1

HCID 22490354Iodophenylhydrazine

Procedure

The starting reactant is phenylhydrazine. The hydrazine group is protected, the aromatic ring is nitrated and subsequently, the nitro-product is chromatographed, reduced to amine, reacted with nitrous acid and sodium iodide to give p-iodo-substituted protected phenylhydrazine. Subsequently it is reacted with hexabutylditin and tetrakis (triphenylphosphine)palladium(0) and then with sodium iodide (NaI125) in the presence of such oxidizing agent as Chloramine-T. The final step, deprotection, gives p-I125 -iodophenylhydrazine.

Workup

customsubsequently, the nitro-product is chromatographed
customreacted with nitrous acid and sodium iodide
customto give p-iodo-substituted

Sources & evidence

ORD record: ord-7eeb57cc517b44d484878c1030bfb583
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05854084

Reaction notes

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