Trifluoroacetic acid → HCID 14500631, compound

HRID 1761586Notes

Reaction equation

HRID 1761586 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1.[O-:15][C:16]#[N:17].[Na+].FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:16]([NH2:17])=[O:15])[CH:9]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 517096Sodium CyanateHCID 14500630HCID 14500630, compound

Product 1

HCID 14500631HCID 14500631, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred solution of 4.4 g (23 mmol) of 1-methyl-2-(3'-aminobenzyl)pyrrole in 400 ml of benzene there were added 3.08 g (47 mmol) of sodium cyanate followed by the dropwise addition of a solution of 3.65 ml (47 mmol) of trifluoroacetic acid in 300 ml of benzene. When the addition was completed, the reaction mixture was stirred at room temperature for 1 hour further and then poured into 500 ml of saturated sodium carbonate solution. The organic phase was separated and the aqueous layer extracted with ethyl acetate (3×500 ml). The combined extracts were washed with water (1×500 ml), dried and evaporated under reduced pressure. The residue was purified by column chromatography on 500 g of silica gel, using methylene chloride-acetone (80:20) as eluant, thus obtaining 5.1 g (90%) of the title compound, 1-methyl-2-(3'-ureidobenzyl)pyrrole, which was recrystallized from acetone-hexane.

Workup

  1. additionWhen the addition
  2. customThe organic phase was separated
  3. extractionthe aqueous layer extracted with ethyl acetate (3×500 ml)
  4. washThe combined extracts were washed with water (1×500 ml)
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on 500 g of silica gel

Sources & evidence

ORD record
ord-dd5543bb08ff493580a3e0b474ec027e
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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