Acetic Anhydride → HCID 19905480, compound

HRID 2371967Notes

Reaction equation

HRID 2371967 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[N:10]([C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([N:25]([OH:27])[CH3:26])=[O:24])=[CH:17][CH:16]=2)[C:11]([CH3:14])=[CH:12][CH:13]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>C(Cl)Cl>[CH3:8][C:9]1[N:10]([C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([N:25]([O:27][C:28](=[O:30])[CH3:29])[CH3:26])=[O:24])=[CH:17][CH:16]=2)[C:11]([CH3:14])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 6439321131817-86-2

Product 1

HCID 19905480HCID 19905480, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.06 g) is added to a mixture of 5.0 g of (E)-3-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-phenyl]-N-hydroxy-N-methyl-2-propenamide in 100 ml of methylene chloride and the mixture is stirred for 15 minutes. Acetic anhydride (2.07 g) is added and the mixture is stirred at room temperature overnight. The reaction mixture is washed with water and sodium bicarbonate solution, the organic layer is separated, treated with charcoal, dried and evaporated to dryness. The residue is crystallized from ethanol, water (1:1) to yield (E)-3-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-phenyl]-N-acetoxy-N-methyl-2-propenamide, m.p. 120°-121°.

Workup

  1. stirringthe mixture is stirred at room temperature overnight
  2. washThe reaction mixture is washed with water and sodium bicarbonate solution
  3. customthe organic layer is separated
  4. additiontreated with charcoal
  5. customdried
  6. customevaporated to dryness
  7. customThe residue is crystallized from ethanol, water (1:1)

Sources & evidence

ORD record
ord-5d28e5e55ad045169d7c65068fb13832
Source dataset
uspto-grants-1992_03
Patent number
US05096919

Reaction notes

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