Triethylamine → HCID 13736042, compound

HRID 2234801Notes

Reaction equation

HRID 2234801 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6](=[NH:8])[NH2:7])[CH3:2].C(N(CC)CC)C.Br[CH:18]([CH3:22])[C:19](=O)[CH3:20]>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:5]1[C:19]([CH3:20])=[C:18]([CH3:22])[NH:8][C:6]=1[NH2:7])=[O:9])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 131422-Butanone, 3-bromo-HCID 4599837Carbamimidoyl-acetic acid ethyl ester

Product 1

HCID 13736042HCID 13736042, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of Carbamimidoyl-acetic acid ethyl ester (0.5 g) in ethyl acetate (6 mL) was added triethylamine (0.5 mL) and mixture was stirred at 5° C. Than 3-Bromo-butan-2-one (0.4 mL) was added under a nitrogen atmosphere and the mixture was refluxed for 1 h. The reaction mixture was then filtered through a medium porosity fitted glass funnel containing a thin layer of silica gel. The filtrate was washed with 100 mL of ethyl acetate and the combined washes were then evaporated under reduced pressure to give (0.25 g, 35%) of 2-Amino-4,5-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester [MH]+=183.

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. filtrationThe reaction mixture was then filtered through a medium porosity
  3. customfitted glass funnel
  4. additioncontaining a thin layer of silica gel
  5. washThe filtrate was washed with 100 mL of ethyl acetate
  6. customthe combined washes were then evaporated under reduced pressure

Sources & evidence

ORD record
ord-0acaa3d719d1456ba7803ba73506e67c
Source dataset
uspto-grants-2010_05
Patent number
US07713966B2

Reaction notes

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