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

HRID 868540Notes

Reaction equation

HRID 868540 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-1,4-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-e9274e4c4fed4362a879e98a886da25c
Source dataset
uspto-grants-1988_10
Patent number
US04780469

Reaction notes

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