Thiosemicarbazide → 4-Acetamido-3-iodobenzaldehyde thiosemicarbazone

HRID 1168146Notes

Reaction equation

HRID 1168146 reaction equation
[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[I:13])(=[O:3])[CH3:2].[NH2:14][NH:15][C:16]([NH2:18])=[S:17]>[Ni]>[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[N:14][NH:15][C:16]([NH2:18])=[S:17])=[CH:7][C:6]=1[I:13])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2723789ThiosemicarbazideHCID 229919464-Acetamido-3-iodobenzaldehyde2×

Product 1

HCID 30022964-Acetamido-3-iodobenzaldehyde thiosemicarbazone

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Iodination of 4-aminobenzonitrile 30 with ICI produces 4-amino-3-iodobenzonitrile 31. Acetylatation of 4-amino-3-iodobenzonitrile 31 results in compound 32, which can be reduced with Raney nickel to form 4-acetamido-3-iodobenzaldehyde 33. Reaction of compound 33 with thiosemicarbazide yields 4-acetamido-3-iodobenzaldehyde thiosemicarbazone 34, as illustrated below.

Sources & evidence

ORD record
ord-580cd3150b984feaa4bf588641c3fa66
Source dataset
uspto-grants-2003_09
Patent number
US06624153B2

Reaction notes

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