1-Methyl-5-nitro-1H-benzimidazole-2-butanoic Acid Ethyl Ester Chemical Properties

Melting point:

100-104°C

Boiling point:

481.0±25.0 °C(Predicted)

Density 

1.30±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Dichloromethane, Ethyl Acetate, Methanol

form 

Solid

pka

3.78±0.10(Predicted)

color 

Brown

InChI

InChI=1S/C14H17N3O4/c1-3-21-14(18)6-4-5-13-15-11-9-10(17(19)20)7-8-12(11)16(13)2/h7-9H,3-6H2,1-2H3

InChIKey

VJVBGSJZBDBEIF-UHFFFAOYSA-N

SMILES

C1(CCCC(OCC)=O)N(C)C2=CC=C([N+]([O-])=O)C=C2N=1

1-Methyl-5-nitro-1H-benzimidazole-2-butanoic Acid Ethyl Ester Usage And Synthesis

Chemical Properties

Light Brown Solid

Uses

1-Methyl-5-nitro-1H-benzimidazole-2-butanoic Acid Ethyl Ester is a Bendamustine intermediate.

Uses

Labelled Bendamustine

Synthesis

157 g (596.4 mmol) of 1-methyl-5-nitro-1H-benzimidazole-2-butanoic acid was suspended in 1374 g of ethanol, 43.8 g of 96% sulfuric acid was added and the reaction mixture was heated to 50 °C. After refluxing the reaction for 10 hours, the mixture was concentrated to a crystalline concentration. The catalytic acid was neutralized with triethylamine and crystallization was promoted by cooling, followed by filtration to collect the precipitate. The product, ethyl 1-methyl-5-nitro-1H-benzimidazole-2-butanoate, was washed with ethanol and dried to give 163 g (559.5 mmol) with a purity of >99% (yield 93.8% of the theoretical value).

References

[1] Patent: US2014/31560, 2014, A1. Location in patent: Paragraph 0101; 0102
[2] Patent: EP2690096, 2014, A1. Location in patent: Paragraph 0073; 0074

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