Toluene → HCID 54724164, compound

HRID 1866879Notes

Reaction equation

HRID 1866879 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]=[C:10]=[O:11].[CH2:12]=[C:13]1[O:17][C:15](=[O:16])[CH2:14]1.[C:18]1(C)[CH:23]=CC=C[CH:19]=1>>[C:13]([C:14]1[C:10](=[O:11])[N:9]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])[C:18]([CH3:23])=[CH:19][C:15]=1[OH:16])(=[O:17])[CH3:12]

Participants

4

Reactant 3

HCID 1140TolueneHCID 12661DiketeneHCID 6045371,3-Dichloro-2-isocyanatobenzene

Product 1

HCID 54724164HCID 54724164, compound

Procedure

A mixture of 2,6 dichlorophenylisocyanate (4.8 g, 0.025 mol), and diketene (4.3 g, 0.05 mol) in toluene (15.0 mL) was heated to reflux for 4 h under an atmosphere of argon. After removal of the solvent in vacuo, the residue was purified by silica gel flash chromatography using EtOAc/hexanes (1:3 v/v). The appropriate fractions, as monitored by ES mass spectrometry (MH+ m/z=312) were combined and concentrated under reduced pressure. The resulting yellow solid (2.3 g) was further purified by reverse-phase HPLC using 10 90% acetonitrile/water gradient (45 min) at a flow rate of 100 mL/min. The appropriate fractions, as monitored by ES mass spectrometry (MH+ m/z=312) were combined and concentrated to half the volume. The solid that separated was extracted with EtOAc (2×25 mL). The combined extracts were washed with water, dried (Na2SO4), filtered, and concentrated to dryness to give the title compound (0.77 g) as a pale yellow powder: 1H-NMR (CD3OD) δ: 7.62 (m, 2H), 7.52 (m, 1H), 6.19 (s, 1H), 2.59 (s, 3H), and 1.96 (6, 3H); ES-MS m/z=312 (MH+); HR-MS, m/z calc C14H12NO3Cl2 312.0189, found 312.0214.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h under an atmosphere of argon
  3. customAfter removal of the solvent in vacuo
  4. customthe residue was purified by silica gel flash chromatography
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting yellow solid (2.3 g) was further purified by reverse-phase
  7. custom10 90% acetonitrile/water gradient (45 min)
  8. concentrationconcentrated to half the volume
  9. customThe solid that separated
  10. extractionwas extracted with EtOAc (2×25 mL)
  11. washThe combined extracts were washed with water
  12. dry with materialdried (Na2SO4)
  13. filtrationfiltered
  14. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-45269eff70674d6588e7abff7e62d3ac
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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