Triethylamine → HCID 54705977, compound

HRID 1869290Notes

Reaction equation

HRID 1869290 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12]CC)=O)=[C:7]([NH:15][C:16]([C:18]3[CH:19]=[N:20][O:21][C:22]=3[CH3:23])=[O:17])[C:6]=2[CH:24]=1.[CH2:25](N(CC)CC)C>O>[C:10]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][CH:2]=[CH:24][C:6]=2[C:7]=1[NH:15][C:16](=[O:17])/[C:18](/[C:19]#[N:20])=[C:22](\[OH:21])/[CH3:23])(=[O:12])[CH3:25]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 11395254HCID 11395254, compound

Product 1

HCID 54705977HCID 54705977, compoundYield 449.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
68 °C

Procedure

To a solution (30 ml) of ethyl 5-bromo-3-[(5-methylisoxazole-4-carbonyl)amino]benzofurane-2-carboxylate (compound of Example 67 described below) (0.2 g, 1.8 mmol) produced according to Example 65 in water-free THF was added triethylamine (2.4 ml, 0.18 mmol), and the reaction mixture was heated at 68° C. for 6 hr and the solvent was evaporated. The residue was poured into ice water, and the mixture was acidified 30 with 5% aqueous hydrochloric acid solution and extracted with CHCl3. The extract was washed with saturated brine and dried. The solvent was evaporated. The residue was recrystallized from acetonitrile to give (Z)-N-(2-acetylbenzofuran-3-yl)-2-cyano-3-hydroxy-2-butenamide as colorless crystals (0.23 g, yield 22.6%).

Workup

  1. customthe solvent was evaporated
  2. additionThe residue was poured into ice water
  3. extractionextracted with CHCl3
  4. washThe extract was washed with saturated brine
  5. customdried
  6. customThe solvent was evaporated
  7. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-5ed1f90fac2c4da386b4c0411a8642d1
Source dataset
uspto-grants-2009_12
Patent number
US07638540B2

Reaction notes

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