1,1'-Carbonyldiimidazole → 5-Methyl-4-nitro-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amide

HRID 583773Notes

Reaction equation

HRID 583773 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][C:14]1[S:18][C:17]([C:19]([OH:21])=O)=[CH:16][C:15]=1[N+:22]([O-:24])=[O:23].[CH2:25]([NH2:35])[C:26]1[CH:34]=[CH:33][C:32]2[O:31][CH2:30][O:29][C:28]=2[CH:27]=1>>[O:31]1[C:32]2[CH:33]=[CH:34][C:26]([CH2:25][NH:35][C:19]([C:17]3[S:18][C:14]([CH3:13])=[C:15]([N+:22]([O-:24])=[O:23])[CH:16]=3)=[O:21])=[CH:27][C:28]=2[O:29][CH2:30]1

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 31107845-Methyl-4-nitrothiophene-2-carboxylic acid

Product 1

HCID 465857615-Methyl-4-nitro-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amideYield 97.6%

Procedure

The title compound was prepared according to the procedure described for Example 2 using carbonyldiimidazole (0.7 g, 4.3 mmol), 5-methyl-4-nitro-thiophene-2-carboxylic acid (0.6 g, 3.2 mmol), and piperonyl amine (0.5 g, 3.3 mmol). Acidification of the aqueous workup mixture with dilute hydrochloric acid prior to filtration afforded 1 g of 5-methyl-4-nitro-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amide. A sample was dissolved in ethyl acetate and filtered through a short column of silica gel to give 5-methyl-4-nitro-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amide; mp 181-183° C.

Workup

  1. customThe title compound was prepared
  2. filtrationAcidification of the aqueous workup mixture with dilute hydrochloric acid prior to filtration

Sources & evidence

ORD record
ord-f8dcaf95ca7443f095de0c47b8082c4d
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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