2-Acetyl-5-iodothiophene → HCID 20531515, compound

HRID 1759632

Reaction equation

HRID 1759632 reaction equation
IC1SC(C(=O)C)=CC=1.[C:10]([C:12]1[S:16][C:15]([C:17](=[O:19])[CH3:18])=[CH:14][CH:13]=1)#[N:11]>>[C:17]([C:15]1[S:16][C:12]([CH2:10][NH2:11])=[CH:13][CH:14]=1)(=[O:19])[CH3:18]

Participants

3

Reactant 2

HCID 965692-Acetyl-5-iodothiopheneHCID 27475655-Acetylthiophene-2-carbonitrile

Product 1

HCID 20531515HCID 20531515, compound

Procedure

Starting with the readily available compound, denoted 2, 5-iodo-2-acetylthiophene ##STR2## and using a procedure described by S. Nishimura and E. Imoto, Nippon Kagaku Zasshi 82, 1411 (1961), incorporated by reference herein, one generates 5-cyano-2-acetylthiophene denoted 3 below, ##STR3## The "blocked" form is then generated according to standard methods. See for example W. S. Johnson et al., J. Amer. Chem. Soc. 78, 6300, (1956), incorporated by reference herein. This results in a compound, denoted 4 below, ##STR4## Compound 4 is then reduced with available methods such as the one described by R. F. Nystrom and W. G. Brown, J. Amer. Chem. Soc. 70, 3738 (1948), incorporated by reference herein, and then "deblocked" (see for example W. S. Johnson et al. above) to give 2-acetyl-5-(aminomethyl)thiophene, 5,: ##STR5## Then using standard Claisen condensation techniques, such as described by J. C. Reid and M. Calvin, J. Amer. Chem. Soc. 72, 2948 (1950), incorporated by reference herein, the chelating ligand 1 is synthesized, abbreviated hereafter as TTFA-NH2.

Workup

  1. customThis results in a compound

Sources & evidence

ORD record
ord-3c53afc2278a4470934a9747cd049c23
Source dataset
uspto-grants-1982_07
Patent number
US04341957

Linked notes

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