Ammonia → 8-(p-Pentylcinnamoyl)amino-1,4-benzodioxane-2-acetamide

HRID 231563Notes

Reaction equation

HRID 231563 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]1[O:10][C:9]2[C:11]([NH:15][C:16](=[O:30])[CH:17]=[CH:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:21][CH:20]=3)=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH2:6]1.[NH3:32]>C(O)C>[CH2:25]([C:22]1[CH:23]=[CH:24][C:19]([CH:18]=[CH:17][C:16]([NH:15][C:11]2[C:9]3[O:10][CH:5]([CH2:4][C:3]([NH2:32])=[O:2])[CH2:6][O:7][C:8]=3[CH:14]=[CH:13][CH:12]=2)=[O:30])=[CH:20][CH:21]=1)[CH2:26][CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 539083158-(p-Pentylcinnamoyl)amino-1,4-benzodioxane-2-acetic acid methyl ester

Product 1

HCID 542031508-(p-Pentylcinnamoyl)amino-1,4-benzodioxane-2-acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8-(p-pentylcinnamoyl)amino-1,4-benzodioxane-2-acetic acid methyl ester (341 mg; synthesized in reference example 3) was dissolved into ethanol which was saturated with ammonia (20 ml). The solution was allowed to stand for 3 days at 100° C. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate=2:1) to give the title compound (191 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (hexane: ethyl acetate=2:1)

Sources & evidence

ORD record
ord-352b5dc880ae449e963b094ffb318c1a
Source dataset
uspto-grants-1989_07
Patent number
US04847275

Reaction notes

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