Water → HCID 11402593, compound

HRID 1581476Notes

Reaction equation

HRID 1581476 reaction equation
C(OC(=O)[NH:10][C:11]1[S:15][C:14]2[C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:17][CH:18]=[C:19]([O:20][CH3:21])[C:13]=2[CH:12]=1)C1C=CC=CC=1.O1CCOCC1.[OH-].[Na+].O>C=C>[CH3:21][O:20][C:19]1[C:13]2[CH:12]=[C:11]([NH2:10])[S:15][C:14]=2[C:16]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 20724759HCID 20724759, compound

Product 1

HCID 11402593HCID 11402593, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6325EthyleneSolvent

Procedure

A stirred solution of (4-methoxy-7-phenyl-benzo[b]thiophen-2-yl)-carbamic acid benzyl ester (1.7 g, 4.36 mmol) in ethylene gylcol and dioxane was heated under reflux with 2N NaOH (20 ml, 9.1 eq) for 4 h. After cooling and addition of water (20 ml) the mixture was extracted with EtOAc (3×25 ml), the combined extracts were washed with brine, dried with Na2SO4 filtered and evaporated. The crude residue was then chromatographed over silica gel eluting with dichloromethane/2N NH3 in MeOH (99:1). This afforded the title compound (668 mg, 60% yield) as a red gum. MS m/e=256.2 (M+)

Workup

  1. temperatureAfter cooling
  2. extractionwas extracted with EtOAc (3×25 ml)
  3. washthe combined extracts were washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude residue was then chromatographed over silica gel eluting with dichloromethane/2N NH3 in MeOH (99:1)

Sources & evidence

ORD record
ord-2dfbe16f9b3b41b096f5d91b556f5f23
Source dataset
uspto-grants-2004_05
Patent number
US06730670B2

Reaction notes

Loading…