Hydrochloric Acid → N-(3,4-diacetoxycinnamoyl)-4-benzyloxy-3,5-dimethylaniline

HRID 728348Notes

Reaction equation

HRID 728348 reaction equation
[CH2:1]([O:8][C:9]1[C:15]([CH3:16])=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:24]([O:27][C:28]1[CH:29]=[C:30]([CH:36]=[CH:37][C:38]=1[O:39][C:40](=[O:42])[CH3:41])[CH:31]=[CH:32][C:33](Cl)=[O:34])(=[O:26])[CH3:25].Cl>CN(C)C=O>[C:24]([O:27][C:28]1[CH:29]=[C:30]([CH:36]=[CH:37][C:38]=1[O:39][C:40](=[O:42])[CH3:41])[CH:31]=[CH:32][C:33]([NH:13][C:12]1[CH:14]=[C:15]([CH3:16])[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([CH3:17])[CH:11]=1)=[O:34])(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 149886364-(Benzyloxy)-3,5-dimethylanilineHCID 545330334-(3-Chloro-3-oxoprop-1-en-1-yl)-1,2-phenylene diacetate

Product 1

HCID 53990996N-(3,4-diacetoxycinnamoyl)-4-benzyloxy-3,5-dimethylanilineYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1.6 g of 4-benzyloxy-3,5-dimethylaniline in 30 ml of dimethylformamide is added under ice-cooling 1.17 g of potassium carbonate, and then a solution of 2.0 g of 3,4-diacetoxycinnamoyl chloride in 10 ml of dimethylformamide is added dropwise at 5° to 7° C., followed by stirring at room temperature for 2 hours. The reaction mixture is poured into ice-water, adjusted to pH 1 with 10 % hydrochloric acid and extracted with ethyl acetate. The extract is washed with water, dried and then concentrated. Recrytallization of the residue from methanol gives 2.64 g of N-(3,4-diacetoxycinnamoyl)-4-benzyloxy-3,5-dimethylaniline.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c3a2eb76549f4d81a22bee9c4532dd42
Source dataset
uspto-grants-1991_09
Patent number
US05047555

Reaction notes

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