Glycerol → HCID 53932050, compound

HRID 1419826Notes

Reaction equation

HRID 1419826 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[NH2:9].II.S(=O)(=O)(O)O.O[CH2:24][CH:25]([CH2:27]O)O>>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:10]([CH:24]=[CH:25][CH:27]=[N:9]2)=[CH:11][C:12]=1[O:13][CH3:14]

Participants

5

Reactant 4

HCID 753GlycerolHCID 807IodineHCID 1118Sulfuric AcidHCID 105603983-(2-(Dimethylamino)ethoxy)-4-methoxyaniline

Product 1

HCID 53932050HCID 53932050, compoundYield 51%

Conditions

Temperature
180 °C

Procedure

3-(2-Dimethylaminoethoxy)-4-methoxyaniline (D14, 200 mg) was treated with glycerol (133 mg) and iodine (5 mg) and to this stirring mixture was added dropwise, concentrated sulphuric acid (267 mg). After the initial exothermic reaction had subsided, the mixture was heated at 180° C. for 1.5 hr. The reaction mixture was cooled and partitioned between 40% aqueous sodium hydroxide and ethyl acetate, the organic phase was dried (Na2SO4) and the solvent evaporated under reduced pressure to leave the title compound as a brown oil (19 mg, 51%).

Workup

  1. additionwas added dropwise
  2. customAfter the initial exothermic reaction
  3. temperatureThe reaction mixture was cooled
  4. custompartitioned between 40% aqueous sodium hydroxide and ethyl acetate
  5. dry with materialthe organic phase was dried (Na2SO4)
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-d4ed40d943f74703b7f5099c2758b6f2
Source dataset
uspto-grants-1999_03
Patent number
US05889022

Reaction notes

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