Oxalic Acid → HCID 178526031, compound

HRID 486053Notes

Reaction equation

HRID 486053 reaction equation
[CH2:1]([N:9]=[C:10]=[S:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH:12]1[CH:16]=[C:15]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[N:14]=[CH:13]1.[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25]>C1(C)C=CC=CC=1.C(O)(C)C>[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25].[CH2:1]([NH:9][C:10]([N:20]1[CH2:19][CH2:18][CH:17]([C:15]2[N:14]=[CH:13][NH:12][CH:16]=2)[CH2:22][CH2:21]1)=[S:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 16741Phenethyl IsothiocyanateHCID 1784208734-(1H-imidazol-4-yl)piperidine

Product 1

HCID 178526031HCID 178526031, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1.63 g (0.01 mol) of phenethyl isothiocyanate in 60 ml of toluene and 1.51 g (0.01 mol) of 4-(4-imidazolyl)piperidine is heated to reflux for 1h 30 min. After cooling, the solution is evaporated under reduced pressure and the residual oil obtained is dissolved in 60 ml of isopropanol in the presence of 1.2 equivalents of oxalic acid. After 30 minutes of heating at 80° C., the white precipitate formed is drained, washed with ether and recrystallised in acetonitrile.

Workup

  1. temperatureAfter cooling
  2. customthe solution is evaporated under reduced pressure
  3. customthe residual oil obtained
  4. customthe white precipitate formed
  5. washwashed with ether
  6. customrecrystallised in acetonitrile

Sources & evidence

ORD record
ord-474f4c34d56c412e9d2b44ede976dcb9
Source dataset
uspto-grants-1994_03
Patent number
US05290790

Reaction notes

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