Acetic Acid → HCID 18355309, compound

HRID 429673Notes

Reaction equation

HRID 429673 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[N:19]([CH3:57])[C:20](=[O:56])[C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([N+:36]([O-])=O)[C:31]=2[NH:39][C:40]([CH2:42][N:43]2[C:47](=[O:48])[C:46]3=[CH:49][CH:50]=[CH:51][CH:52]=[C:45]3[C:44]2=[O:53])=O)=[O:29])=[C:23]([O:54][CH3:55])[CH:22]=1)=[O:5])[CH3:2].C(O)(=O)C>C(O)C.[Fe]>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[N:19]([CH3:57])[C:20](=[O:56])[C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]2[C:31]3[N:39]=[C:40]([CH2:42][N:43]4[C:47](=[O:48])[C:46]5=[CH:49][CH:50]=[CH:51][CH:52]=[C:45]5[C:44]4=[O:53])[NH:36][C:32]=3[CH:33]=[CH:34][CH:35]=2)=[O:29])=[C:23]([O:54][CH3:55])[CH:22]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 18355313HCID 18355313, compound

Product 1

HCID 18355309HCID 18355309, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-[2-(5-ethoxycarbonylpent-1-yloxy)-4-methylphenyl]-3-methoxy-N-methyl-4-(3-nitro-2-phthalimidomethylcarbonylaminophenyl)carbonylaminobenzamide (3.96 g), iron powder (1.42 g) and acetic acid (3.05 g) in ethanol (50 ml) was refluxed for 4 hours and the solvent was removed under reduce pressure. The residue was stirred in a mixture of chloroform (100 ml) and saturated aqueous sodium hydrogen carbonate (100 ml) for 30 minutes and the solution was filtered through a bed of celite. The organic phase was separated and washed with brine. The solution was dried over magnesium sulfate and the solvent was evaporated in vacuo. The residue was solidified with diethyl ether to give N-[2-(5-ethoxycarbonylpent-1-yloxy)-4-methylphenyl]-3-methoxy-N-methyl-4-(2-phthalimidomethyl-1H-benzimidazol-4-yl)carbonylaminobenzamide (3.64 g).

Workup

  1. temperaturewas refluxed for 4 hours
  2. customthe solvent was removed
  3. filtrationthe solution was filtered through a bed of celite
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialThe solution was dried over magnesium sulfate
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-3df84b45c557438fa497661d2b940ace
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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