Dicyclohexylcarbodiimide → 4-(3-Methoxycinnamoyl)amino-2,6-dimethyl-phenol

HRID 728347Notes

Reaction equation

HRID 728347 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=1)[CH:16]=[CH:17][C:18](O)=[O:19].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>O1CCCC1.C(OCC)(=O)C>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=1)[CH:16]=[CH:17][C:18]([NH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1)=[O:19]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 826684-Amino-2,6-dimethylphenolHCID 871552-Propenoic acid, 3-(3-methoxyphenyl)-

Product 1

HCID 536624954-(3-Methoxycinnamoyl)amino-2,6-dimethyl-phenolYield 68.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under argon gas stream, to a solution of 600 mg of 4-amino-2,6-dimethylphenol in 20 ml of tetrahydrofuran is added under ice-cooling 779 mg of 3-methoxycinnamic acid, and then 902 mg of dicyclohexylcarbodiimide and 118 mg of 1-hydroxybenzotriazole are added, followed by stirring at room temperature overnight. After ethyl acetate is added to the reaction mixture, the mixture is washed successively with 10 % hydrochloric acid, water, 5 % sodium hydrogen carbonate and water, and dried, followed by concentration. The residue is recrystallized from ethyl acetate-n-hexane to give 890 mg of 4-(3-methoxycinnamoyl)amino-2,6-dimethyl-phenol.

Workup

  1. washthe mixture is washed successively with 10 % hydrochloric acid, water, 5 % sodium hydrogen carbonate and water
  2. customdried
  3. concentrationfollowed by concentration
  4. customThe residue is recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-4e4ed0753c1748ee950f196a2144001c
Source dataset
uspto-grants-1991_09
Patent number
US05047555

Reaction notes

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