Formic Acid → HCID 13019461, compound

HRID 2285732Notes

Reaction equation

HRID 2285732 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]2[NH:15][CH:16]=[CH:17][N:18]=2)[CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[CH:19](O)=[O:20]>C1(C)C=CC=CC=1>[NH:18]1[CH:17]=[CH:16][N:15]=[C:14]1[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][CH:19]=[O:20])=[CH:3][CH:4]=1)[CH2:9][CH2:10][N:11]([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 13019470HCID 13019470, compound

Product 1

HCID 13019461HCID 13019461, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(4-aminophenyl)-N,N-dimethyl-3-(imidazol-2-yl)propanamine (0.8 g), formic acid (2 ml) and toluene (50 ml) was boiled under reflux for 2 days in a Dean and Stark apparatus. Solvent was removed and the residue partitioned between 2 N sodium carbonate (25 ml) and ethyl acetate (3×50 ml). The extracts were dried (Na2SO4) and concentrated to a white solid. Recrystallisation from ethyl acetate gave the title compound, m.p. 142°-144°, (0.46 g). ν max (CHBr3) 3445, 3420,3390 (NH), 1690(CO), 1500, 2780 and 2820 cm-1.

Workup

  1. temperatureunder reflux for 2 days in a Dean and Stark apparatus
  2. customSolvent was removed
  3. customthe residue partitioned between 2 N sodium carbonate (25 ml) and ethyl acetate (3×50 ml)
  4. dry with materialThe extracts were dried (Na2SO4)
  5. concentrationconcentrated to a white solid
  6. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-5834ba30b39247e185b6c730fc86778f
Source dataset
uspto-grants-1982_04
Patent number
US04324792

Reaction notes

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