Hydrochloric Acid → HCID 66987155, compound

HRID 555276Notes

Reaction equation

HRID 555276 reaction equation
C[O:2][C:3]([C:5]1[CH:21]=[CH:20][C:8]2[N:9]([CH2:12][CH2:13][O:14][CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:10]=[N:11][C:7]=2[CH:6]=1)=[O:4].[Li+].[OH-].Cl>C1COCC1.O>[CH3:19][S:16]([CH2:15][O:14][CH2:13][CH2:12][N:9]1[C:8]2[CH:20]=[CH:21][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[N:11]=[CH:10]1)(=[O:17])=[O:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66987468HCID 66987468, compound

Product 1

HCID 66987155HCID 66987155, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Methanesulfonylmethoxyethyl)-1-H-benzimidazole-5-carboxylic acid methyl ester (1.0 g, 3.2 mmoles) was dissolved in THF (5 mL). A solution of LiOH (0.38 g, 16 mmol) in water was added and the mixture stirred vigorously for 1 h. The reaction was acidified with 2N HCl to pH 2 at 5-10° C. It was then filtered to give 0.8 g (84%) of 1-(2-methanesulfonylmethoxyethyl)-1H-benzoimidazole-5-carboxylic acid. 1H NMR (300 MHz, DMSO-d6) δ 2.9 (s, 3H), 4.2 (t, 2H), 4.5 (t, 2H), 4.65 (s, 2H), 7.75 (d, 1H), 7.9 (dd, 1H), 8.25 (d, 1H), 8.35 (s, 1H), 12.7 (s, 1H)

Workup

  1. filtrationIt was then filtered

Sources & evidence

ORD record
ord-2c658337d5244c8480cbcebfe941fc8c
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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