Water → HCID 22729240, compound

HRID 2085194Notes

Reaction equation

HRID 2085194 reaction equation
O=[C:2]([CH2:18][CH3:19])[CH2:3][NH:4][C:5]([C:7]1[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[C:15]([O:16][CH3:17])[C:9]=2[CH:8]=1)=[O:6].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.O>C1COCC1>[CH2:18]([C:2]1[O:6][C:5]([C:7]2[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([O:16][CH3:17])[C:9]=3[CH:8]=2)=[N:4][CH:3]=1)[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 22729001HCID 22729001, compound

Product 1

HCID 22729240HCID 22729240, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-oxobutyl)-4-methoxybenzo(b)furan-2-carboxamide (2.00 g) in THF (60 ml) was added Burgess reagent (7.30 g), and the mixture was stirred with refluxing. Water (200 ml) was added to the reaction mixture and the mixture was extracted with ether. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound (1.56 g) as colorless crystals, melting point 88-87° C.

Workup

  1. temperaturewith refluxing
  2. extractionthe mixture was extracted with ether
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b495a56a11184689b5b1ebf668893786
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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