Methanol → HCID 66986996, compound

HRID 555279Notes

Reaction equation

HRID 555279 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])=[C:6]([N+:17]([O-])=O)[CH:5]=1.[CH3:21]O>[Pd]>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:21]=[N:17][C:6]=2[CH:5]=1)=[O:20]

Participants

4

Reactant 2

HCID 887MethanolHCID 66987535HCID 66987535, compound

Product 1

HCID 66986996HCID 66986996, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-(2-Methanesulfonyl-ethylamino)-3-nitro-benzoic acid methyl ester (1.63 g, 5.40 mmol) was dissolved in methanol, and 10% Pd/C (150 mg) was added to it under N2 atmosphere. The reaction mixture was then hydrogenated at 1 atmospheric pressure at room temp for 2 h. It was filtered through celite and the filtrate concentrated to yield the desired product. The crude material (1.32 g, 4.85 mmol) was taken in formic acid (10 mL) and allowed to stir at 50° C. for 4 h. The reaction mass was concentrated, diluted with water and extracted with EtOAc. The organic layers were washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated to give 1-(2-methanesulfonylethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester (77%). 1H NMR (300 MHz, DMSO-d6).

Workup

  1. filtrationIt was filtered through celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-0d38758896a4493f8ea206c1b7601825
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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