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Purification of 5-amino-3-[4-(3-di-n-butylaminopropoxy)benzoyl]-2-n-butylbenzofuran

IP.com Disclosure Number: IPCOM000237249D
Publication Date: 2014-Jun-10
Document File: 1 page(s) / 23K

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Abstract

Provided is a process for the purification of 5-amino-3-[4-(3-di-n-butylaminopropoxy)benzoyl]-2-n-butylbenzofuran

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Purification of 5-amino-3-[4-(3-di-n-butylaminopropoxy)benzoyl]-2-n-butylbenzofuran

Provided is a process for the purification of 5-amino-3-[4-(3-di-n-butylaminopropoxy)benzoyl]-2- n-butylbenzofuran

Preparation of 5-amino-3-[4-(3-di-n-butylaminopropoxy)benzoyl]-2-n-butylbenzofuran dioxalate

O

O

H2N

OC3H6N(C4H9)2

COOH COOH COOH

COOH

OC3H6N(C4H9)2

H2N

O

O

A solution of 77.6 g (0.61 mols) of oxalic acid dihydrate in methyl ethyl ketone(400 ml) was heated to 60ºC until total dissolution. The acid solution was added into the stirred solution of 5- amino-3-[4-(3-di-n-butylaminopropoxy)benzoyl]-2-n-butylbenzofuran (134 g, 0.28 mols) in ethyl acetate (1485 ml) at 60ºC.

The reaction mixture was heated to reflux for 1h. The slurry obtained was cooled to 5ºC in 2h. The precipitated solids were filtered and washed with methyl ethyl ketone (200 ml).

The dioxalate salt crude was diluted with a mixture of water (369 ml) and methyl ethyl ketone (1844 ml). The slurry was heated to reflux until total dissolution and then cooled to 5ºC in 2h. The solid was isolated by filtration, washed with methyl ethyl ketone (184 ml) and dried at 50ºC. 162.9 g of purified 5-amino-3-[4-(3-di-n-butylaminopropoxy)benzoyl]-2-n-butylbenzofuran dioxalate was obtained (88% yield).

Preparation of 5-amino-3-[4-(3-di-n-butylaminopropoxy)benzoyl]-2-n-butylbenzofuran

OC3H6N(C4H9)2

COOH COOH COOH

COOH

O

O

OC3H6N(C4H9)2

H2N

H2N

O

O

An aqueous solution of K2CO3 was added to a suspension of 5-amino-3-[4-...