Toluene → HCID 54724196, compound

HRID 1831890Notes

Reaction equation

HRID 1831890 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=[O:10].[CH2:11]=[C:12]1[O:16][C:14](=[O:15])[CH2:13]1.C(N(CC)CC)C.[C:24]1(C)[CH:29]=CC=C[CH:25]=1>>[C:12]([C:13]1[C:9](=[O:10])[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:24]([CH3:29])=[CH:25][C:14]=1[OH:15])(=[O:16])[CH3:11]

Participants

5

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 12661DiketeneHCID 76833Chlorophenyl isocyanate

Product 1

HCID 54724196HCID 54724196, compound

Procedure

A mixture of 2-chlorophenylisocyanate (3.0 g, 19.53 mmol), and diketene (3.3 g, 39.28 mmol) in toluene (10.0 mL) containing triethylamine (0.05 mL) was heated to reflux for 6 h, under an atmosphere of argon. Toluene was distilled in vacuo and the resulting residue was purified by silica gel flash chromatography using 25% EtOAc in hexanes as the eluent to afford the title compound (0.85 g, see ref: Heterocycles 27 (9), 2063, 1988.) as a pale yellow solid: 1H-NMR (CD3OD) δ: 7.63 (m, 1H), 7.52 (m, 2H), 7.4 (m, 1H), 6.14 (s, 1H), 2.58 (s, 3H), and 1.95 (s, 3H); ES-MS m/z=278 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 h, under an atmosphere of argon
  3. distillationToluene was distilled in vacuo
  4. customthe resulting residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-81b4de200f7d4859a82bdc26b6bbc430
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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