Potassium Carbonate → 3-Oxo-2,3-dihydro-1H-inden-5-yl ethyl(methyl)carbamate

HRID 1454054Notes

Reaction equation

HRID 1454054 reaction equation
[CH2:1]([N:3]([CH3:7])[C:4](Cl)=[O:5])[CH3:2].[OH:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][C:15]2=[O:18])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:18]=[C:15]1[C:16]2[C:12](=[CH:11][CH:10]=[C:9]([O:8][C:4](=[O:5])[N:3]([CH2:1][CH3:2])[CH3:7])[CH:17]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70206596-Hydroxy-1-indanoneHCID 11240471N-Ethyl-N-methylcarbamoyl chloride

Product 1

HCID 117156083-Oxo-2,3-dihydro-1H-inden-5-yl ethyl(methyl)carbamateYield 81.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethylmethyl carbamyl chloride (15.5 g, 127.57 mmol) was added to a stirred suspension of 6-hydroxy-1-indanone (17.2 g, 116.1 mmol) and potassium carbonate (31.8 g, 188 mmol) in acetonitrile (800 mL) at room temperature over a period of 15 minutes. The reaction mixture was heated to reflux and refluxed for 18 hours. The reaction mixture was cooled to ambient temperature, the solvent evaporated and the residue was diluted with water (250 mL) and extracted three times with toluene (250 mL). The combined organic phase was dried on MgSO4 and toluene was evaporated in a rotary evaporator. The crude crystalline product was purified by crystallization from 2-propanol (200 mL), collected by filtration, and dried under vacuum at 50° C. to afford the title compound (22 g, 81.5%). 1H NMR (300 MHz, CDCl3) δ ppm 7.47-7.44 (2H, m, Ar), 7.36 (1H, dd, J 8.4 and 2.1, Ar), 3.52-3.37 (2H, m, NCH2CH3), 3.14-3.108 [2H, m, OCCH2CH2 and incl. NCH3 (two rotamers), at 3.08 and 2.99 (3H, s, Me)], 2.74-2.71 (2H, m, OCCH2 CH2) and 1.25 and 1.19 (two rotamers) (3H, two triplets, J6.9). Mass Spectrum (FAB+) [MH+]=234

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperaturerefluxed for 18 hours
  4. customthe solvent evaporated
  5. additionthe residue was diluted with water (250 mL)
  6. extractionextracted three times with toluene (250 mL)
  7. dry with materialThe combined organic phase was dried on MgSO4 and toluene
  8. customwas evaporated in a rotary evaporator
  9. customThe crude crystalline product was purified by crystallization from 2-propanol (200 mL)
  10. filtrationcollected by filtration
  11. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-16af6f32977440dd8e1ccaf719bd7447
Source dataset
uspto-grants-2009_01
Patent number
US07476757B2

Reaction notes

Loading…