Formic Acid → HCID 13881467, compound

HRID 1164462Notes

Reaction equation

HRID 1164462 reaction equation
C(O[C:4](=[O:6])C)=O.C(O)=O.[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[N:18]1[CH2:22][CH2:21][N:20]([C:23]2[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:30])[C:19]1=[NH:31].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C>[CH3:30][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:23]=1[N:20]1[CH2:21][CH2:22][N:18]([C:12]2[C:11]([CH3:10])=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:17])[C:19]1=[N:31][CH:4]=[O:6]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 75269Acetic-formic anhydrideHCID 516892Sodium BicarbonateHCID 112040802-Imidazolidinimine, 1,3-bis(2,6-dimethylphenyl)-

Product 1

HCID 13881467HCID 13881467, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of 7.5 g (85 mmoles) of acetyl formate (a mixed anhydride of formic acid and acetic acid) in 30 ml of dry chloroform is added dropwise, at room temperature, to a solution of 5.0 g (17.0 mmoles) of 1,3-bis(2',6'-dimethylphenyl)-2-imino-imidazolidine, prepared as described in Method (a) of Example 1, in 50 ml of dry chloroform. The resulting mixture is stirred at 45° to 50° C. for 4 hours, thereafter it is cooled with ice, and 10 ml of a 10% aqueous sodium hydrogencarbonate solution are added dropwise to the stirred mixture at a temperature not exceeding +10° C. The aqueous phase is separated, the chloroform phase is washed thrice with 50 ml of water each, dried over anhydrous sodium sulfate, filtered, and the solvent is evaporated under reduced pressure, 4.6 g (84.2%) of 1,3-bis(2',6'-dimethylphenyl)-2-formylimino-imidazolidine are obtained; the product melts at 306°-308° C. after recrystallization from methanol.

Workup

  1. customprepared
  2. additionare added dropwise to the stirred mixture at a temperature not
  3. customexceeding +10° C
  4. customThe aqueous phase is separated
  5. washthe chloroform phase is washed thrice with 50 ml of water each,
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe solvent is evaporated under reduced pressure, 4.6 g (84.2%) of 1,3-bis(2',6'-dimethylphenyl)-2-formylimino-imidazolidine
  9. customare obtained
  10. customthe product melts at 306°-308° C. after recrystallization from methanol

Sources & evidence

ORD record
ord-3edf31f04aec40289f1ff4f70836e81c
Source dataset
uspto-grants-1983_01
Patent number
US04369325

Reaction notes

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