4-Methylamino-3-chloracetamidobenzoic acid-n-(n-propyl)-n-(2-ethoxycarbonylethyl)amide → 2-Chloromethyl-1-methylbenzimidazol-5-yl-carboxylic acid-n-(n-propyl)-n-(2-ethoxycarbonylethyl)amide

HRID 50231Notes

Reaction equation

HRID 50231 reaction equation
[CH2:1]([N:4]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:5](=[O:19])[C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH3:13])=[C:8]([NH:14][C:15](=O)[CH2:16][Cl:17])[CH:7]=1)[CH2:2][CH3:3]>C(O)(=O)C>[CH2:1]([N:4]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:5]([C:6]1[CH:11]=[CH:10][C:9]2[N:12]([CH3:13])[C:15]([CH2:16][Cl:17])=[N:14][C:8]=2[CH:7]=1)=[O:19])[CH2:2][CH3:3]

Participants

3

Reactant 1

HCID 184124094-Methylamino-3-chloracetamidobenzoic acid-n-(n-propyl)-n-(2-ethoxycarbonylethyl)amide

Product 1

HCID 184123762-Chloromethyl-1-methylbenzimidazol-5-yl-carboxylic acid-n-(n-propyl)-n-(2-ethoxycarbonylethyl)amide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.6 g (4.3 mmol) of 4-methylamino-3-chloracetamidobenzoic acid-N-(n-propyl)-N-(2-ethoxycarbonylethyl)amide were heated to 100° C. in 25 mL of acetic acid for 30 minutes. Then the solvent was distilled off, the crude product was taken up in 40 mL methylene chloride/ethanol (9:1) and washed with 20 mL saturated sodium hydrogen carbonate solution. The organic phase was dried with sodium sulfate and evaporated down. Yield: 1.5 g (100% of theory) of brown oil; Rf value: 0.63 (silica gel; ethyl acetate/ethanol/ammonia=90:10:1).

Workup

  1. distillationThen the solvent was distilled off
  2. washwashed with 20 mL saturated sodium hydrogen carbonate solution
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. customevaporated down

Sources & evidence

ORD record
ord-d0852ca934d34e4194c5c36eb775733c
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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