Trifluoroacetic acid → HCID 14500594, compound

HRID 1761596Notes

Reaction equation

HRID 1761596 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:12]1[C:16]([CH2:17][CH2:18][CH3:19])=[CH:15][CH:14]=[C:13]1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH2:27])[CH:22]=1)[CH2:9][CH2:10][CH3:11].[O-:28][C:29]#[N:30].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.CO>[CH2:8]([N:12]1[C:16]([CH2:17][CH2:18][CH3:19])=[CH:15][CH:14]=[C:13]1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][C:29]([NH2:30])=[O:28])[CH:22]=1)[CH2:9][CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 517096Sodium CyanateHCID 14500593HCID 14500593, compound

Product 1

HCID 14500594HCID 14500594, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 11.4 ml (148 mmol) of trifluoroacetic acid in 100 ml of methylene chloride was added dropwise to a mixture of 20 g (74 mmol) of 1-butyl-2-(3'-aminobenzyl)-5-propylpyrrole dissolved in 80 ml of methylene chloride, 20 ml of methanol, and 9.6 g (148 mmol) of sodium cyanate, at room temperature and under stirring. The reaction mixture was stirred for an hour further, poured into 500 ml of saturated sodium carbonate solution and extracted with 200 ml of methylene chloride and 200 ml of ethyl acetate. The combined extracts were washed with water, dried and evaporated under reduced pressure. The residue was purified by column chromatography on 500 g of silica gel, using methylene chloride-methanol (95:5) as eluant, to produce 21 g (91%) of the title compound, 1-butyl-2-(3'-ureidobenzyl)-5-propylpyrrole, which was recrystallized from acetone-hexane.

Workup

  1. extractionextracted with 200 ml of methylene chloride and 200 ml of ethyl acetate
  2. washThe combined extracts were washed with water
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on 500 g of silica gel

Sources & evidence

ORD record
ord-ea8505ad12e34bb088fac83cf9fa8c41
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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