Trifluoroacetic acid → HCID 14500636, compound

HRID 1761589Notes

Reaction equation

HRID 1761589 reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1)[CH3:2].[O-:16][C:17]#[N:18].[Na+].FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.CO>[CH2:1]([N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:17]([NH2:18])=[O:16])[CH:10]=1)[CH3:2]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 517096Sodium CyanateHCID 14500635HCID 14500635, compound

Product 1

HCID 14500636HCID 14500636, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

1-Ethyl-2-(3'-aminobenzyl)pyrrole 5.6 g (28 mmol) was dissolved in a mixture of 500 ml of methylene chloride and 100 ml methanol; 3.92 g (60 mmol) of sodium cyanate were added to the solution and thereafter, in a dropwise fashion and at room temperature, 4.6 ml (59 mmol) of trifluoroacetic acid in 100 ml of methylene chloride. When the addition was completed, the resulting mixture was stirred for 72 hours, 10 g (90 mmol) of sodium carbonate were added thereto, the mixture stirred for 15 minutes and the solvent evaporated under reduced pressure. The residue was purified by column chromatography on 300 g of silica gel, using methylene chloride-acetone (85:15) as eluant, to produce 4.44 g (65%) of the title compound, 1-ethyl-2-(3'-ureidobenzyl)pyrrole, which was recrystallized from acetone-hexane.

Workup

  1. customat room temperature
  2. additionWhen the addition
  3. stirringthe mixture stirred for 15 minutes
  4. customthe solvent evaporated under reduced pressure
  5. customThe residue was purified by column chromatography on 300 g of silica gel

Sources & evidence

ORD record
ord-e7255f9becbc4f248efe1478c9d10c40
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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