Chlorosuccinimide → 5-Chloro-2-(1-n-butyl-1-methoxymethyleneamino)thiophene-3-carboxylic-acid propylamide

HRID 650932Notes

Reaction equation

[CH2:1]([NH:4][C:5]([C:7]1[CH:11]=[CH:10][S:9][C:8]=1[N:12]=[C:13]([CH2:16][CH2:17][CH2:18][CH3:19])[O:14][CH3:15])=[O:6])[CH2:2][CH3:3].[Cl:20]N1C(=O)CCC1=O>N1C=CC=CC=1>[CH2:1]([NH:4][C:5]([C:7]1[CH:11]=[C:10]([Cl:20])[S:9][C:8]=1[N:12]=[C:13]([CH2:16][CH2:17][CH2:18][CH3:19])[O:14][CH3:15])=[O:6])[CH2:2][CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

In a sulfonation flask 0.85 g 2-(1-n-butyl-1-methoxymethyleneamino)thiophene-3-carboxylic-acid propylamide are added with stirring to 10 ml absolute pyridine. The internal temperature is then raised to 60° C. and 0.5 g of N-chlorosuccinimide (NCS) are added in two portions. After stirring for 1 hour at 60° C., the pyridine is removed in a water jet vacuum. The residue is taken up in ethylacetate and the organic phase is washed twice with water. After drylng of the organic phase, the solvent is removed in a water jet vacuum and the raw material purified by column chromatography over silica gel (eluant:hexane/ethylacetate=3:1). Yield: 0.6 g 5-Chloro-2-(1-n-butyl-1-methoxymethyleneamino)thiophene-3-carboxylic-acid propylamide in the form of brownish crystalls; m.p. 110-112° C.

Workup

customthe pyridine is removed in a water jet vacuum
washthe organic phase is washed twice with water
customthe solvent is removed in a water jet vacuum
customthe raw material purified by column chromatography over silica gel (eluant:hexane/ethylacetate=3:1)

Sources & evidence

ORD record: ord-1d0b0a666ba44a38ba06accdb8b379fd
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06277858B1

Reaction notes

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