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

HRID 387760Notes

Reaction equation

HRID 387760 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-06ebefdee33a49a2828e4088b678f774
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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