Water → 8-(p-Pentylcinnamoyl)amino-1,4-benzodioxane-2-acetonitrile

HRID 2210410Notes

Reaction equation

HRID 2210410 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:14]([C:19]1[CH:43]=[CH:42][C:22]([CH:23]=[CH:24][C:25]([NH:27][C:28]2[C:33]3[O:34][CH:35]([CH2:38][C:39]([NH2:41])=O)[CH2:36][O:37][C:32]=3[CH:31]=[CH:30][CH:29]=2)=[O:26])=[CH:21][CH:20]=1)[CH2:15][CH2:16][CH2:17][CH3:18].N1C=CC=CC=1.O>C1COCC1>[CH2:14]([C:19]1[CH:20]=[CH:21][C:22]([CH:23]=[CH:24][C:25]([NH:27][C:28]2[C:33]3[O:34][CH:35]([CH2:38][C:39]#[N:41])[CH2:36][O:37][C:32]=3[CH:31]=[CH:30][CH:29]=2)=[O:26])=[CH:42][CH:43]=1)[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 542031508-(p-Pentylcinnamoyl)amino-1,4-benzodioxane-2-acetamide

Product 1

HCID 545344778-(p-Pentylcinnamoyl)amino-1,4-benzodioxane-2-acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trifluoroacetic anhydride (0.1 m) was added to a solution of 8-(p-pentylcinnamoyl)amino-l,4-benzodioxane-2-acetamide (191 mg; synthesized in reference example 4) in THF (10 ml) cooling with ice. And pyridine (0.02 ml) was added to the mixture. After stirring for 10 min, the mixture was poured into water. The mixture was extracted with ethyl acetate. The extract was dried, concentrated under reduced pressure to give the title compound.

Workup

  1. temperaturecooling with ice
  2. extractionThe mixture was extracted with ethyl acetate
  3. customThe extract was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-322e3941834c4814a1536a801e8eac28
Source dataset
uspto-grants-1995_10
Patent number
US05459134

Reaction notes

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