HCID 14933665, compound → Methyl 4-nitro-5-propylthiophene-2-carboxylate

HRID 1826547Notes

Reaction equation

HRID 1826547 reaction equation
C(C1C=NC(C2C=CC(O)=CC=2)=NC=1)CCCCCCCCCC.FC1C=C(C(O)=O)SC=1CCC.[CH2:37]([C:40]1[S:44][C:43]([C:45]([O:47][CH3:48])=[O:46])=[CH:42][CH:41]=1)[CH2:38][CH3:39].[N+:49]([O-])([OH:51])=[O:50].OS(O)(=O)=O>>[N+:49]([C:41]1[CH:42]=[C:43]([C:45]([O:47][CH3:48])=[O:46])[S:44][C:40]=1[CH2:37][CH2:38][CH3:39])([O-:51])=[O:50]

Participants

5

Reactant 4

HCID 14933665HCID 14933665, compoundHCID 22134237HCID 22134237, compoundHCID 71777668Sulfuric acid, mixt. with nitric acidHCID 1356196824-(5-Undecylpyrimidin-2-yl)phenol

Product 1

HCID 13205562Methyl 4-nitro-5-propylthiophene-2-carboxylate

Procedure

4.9 g of 4-(5-undecyl-pyrimidin-2-yl)phenol, 2.0 g of 4-fluoro-5-propyl-thiophene-2-carboxylic acid (prepared in accordance with Scheme 1 by nitrating methyl 5-propyl-thiophene-2-carboxylate in HNO3/H2SO4 to form methyl 4-nitro-5-propyl-thiophene-2-carboxylate, followed by reduction of the latter by means of Sn/HCl to give the corresponding amino compound, conversion of the latter into the diazonium tetrafluoroborate, thermolysis and, finally, hydrolysis) and 2.1 g of dicyclohexylcarbodiimide are stirred for 24 h in 50 ml of dichloromethane at room temperature. Filtration, removal of the dichloromethane by distillation, purification by chromatography (silica gel; dichloromethane/heptane) and recrystallization from acetonitrile affords the target compound as colorless crystals.

Sources & evidence

ORD record
ord-12fb2a2713d84c9c8db2bf458e9a45f4
Source dataset
uspto-grants-2006_05
Patent number
US07052742B1

Reaction notes

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