Acetic Acid → HCID 23080931, compound

HRID 541061Notes

Reaction equation

HRID 541061 reaction equation
[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(O)(=O)C.[CH:16](OCC)(OCC)[O:17][CH2:18][CH3:19]>O>[CH2:18]([O:17][C:16]1[NH:11][C:10]2[CH:9]=[CH:8][CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]=2[N:1]=1)[CH3:19]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 31214Ethyl orthoformateHCID 1980692,3-Diaminobenzoic acid

Product 1

HCID 23080931HCID 23080931, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 g of 2,3-diaminobenzoic acid is dissolved into 20 ml of glacial acetic acid. Triethyl orthoformate (2.1 eq.) is added into the above mixture at temperature of 0° C.; and to stir it for 2 hours at temperature of 0˜5° C.; and 150 ml of water is added into it, and then to isolate and filter to produce 2-ethoxy-1H-benzimidazole-4-formic acid. The yield is about 89%. 2-ethoxy-1H-benzimidzzole-4-formic acid is added into 15 ml of thionyl chloride, and to react for 60 minutes, and after end of the reaction completely, and (L)-2-amino-1-p-nitrophenyl-1,3-propylene glycol (1.1 eq) is added into the reaction mixture under stirring for 2 hours at the room temperature, and then to filter the inorganic salt, and evaporate the solvent to dry, to obtain the final product of (L)-2-ethoxy-1H-benzimidazole-4-[N-(1-hydroxymethyl-2-p-nitrophenylhydroxyethyl)amide. The yield is about 91%. Using the same process to prepare the compounds in Table 3.

Workup

  1. customto isolate
  2. filtrationfilter

Sources & evidence

ORD record
ord-f1da2a94e14c4644adda2b1e6881fda8
Source dataset
uspto-grants-2014_10
Patent number
US08871946B2

Reaction notes

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