Ethanol → ethyl 2-amino-5-(4-benzyloxyphenyl)-1H-pyrrole-3-carboxylate

HRID 1010147Notes

Reaction equation

HRID 1010147 reaction equation
C(O)C.Cl.[C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])(=[NH:7])[NH2:6].[O-]CC.[Na+].[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=O)[CH2:33]Br)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[CH2:12]([O:11][C:9]([C:8]1[CH:33]=[C:32]([C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:27][CH:28]=2)[NH:7][C:5]=1[NH2:6])=[O:10])[CH3:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-oneHCID 15555354Ethyl 2-carbamimidoylacetate hydrochloride

Product 1

HCID 22936919ethyl 2-amino-5-(4-benzyloxyphenyl)-1H-pyrrole-3-carboxylateYield 103.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After adding 700 ml of ethanol to 50.7 g of ethyl 2-amidinoacetate hydrochloride (a publicly known compound described in Liebigs Ann. Chem., 1895(1977)), the mixture was stirred at room temperature, 22.3 g of sodium ethoxide (1 equivalent with respect to ethyl 2-amidinoacetate hydrochloride) was added, and the mixture was stirred for 15 minutes under a nitrogen atmosphere. To this there was added 49.9 g of 1-(4-benzyloxyphenyl)-2-bromoethanone (publicly known compound described in Journal of Heterocyclic Chemistry, vol. 2, 310(1965) and Journal of Medicinal Chemistry, vol. 17, 55(1974)), and the mixture was stirred for 36 hours at room temperature under a nitrogen atmosphere. Water was added, ethyl acetate was used for liquid separation and extraction, and then the organic layer was dried over sodium sulfate and concentrated to dryness to obtain 56.7 g of the title compound.

Workup

  1. stirringthe mixture was stirred for 15 minutes under a nitrogen atmosphere
  2. stirringwas stirred for 36 hours at room temperature under a nitrogen atmosphere
  3. customethyl acetate was used for liquid separation and extraction
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c0d73205437148799dbebe2f427835ea
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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