Chloroform → HCID 57428968, compound

HRID 1842580Notes

Reaction equation

HRID 1842580 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=O)[C:5]2[CH:10]=[C:9]([CH3:11])[O:8][C:6]=2[N:7]=1.O=P(Cl)(Cl)[Cl:15].C(Cl)(Cl)Cl.CCCCCC>C(OC(=O)C)(=O)C>[Cl:15][C:4]1[C:5]2[CH:10]=[C:9]([CH3:11])[O:8][C:6]=2[N:7]=[C:2]([CH3:1])[N:3]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8058HexaneHCID 24813Phosphorus oxychlorideHCID 57428967HCID 57428967, compound

Product 1

HCID 57428968HCID 57428968, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a 50 mL flask was added 4 (1.64 g, 10 mmol) and 10 mL POCl3. The resulting mixture was refluxed for 2 h, and the solvent was removed under reduced pressure to afford a dark residue. To this was added 30 mL of CHCl3 and 3 g of silica gel. The solvent was evaporated to afford a plug. Column chromatography of the plug with hexane:acetyl acetate=20:1 as eluent afford 1.55 g (85%) of 5 as a yellow solid: TLC Rf0.26 (Hexane/EtOAC 15:1); mp 47.6-48.1° C.; 1H NMR (DMSO-d6) δ 2.48 (s, 3 H) 2.63 (s, 3 H), 6.77 (s, 1 H).

Workup

  1. temperatureThe resulting mixture was refluxed for 2 h
  2. customthe solvent was removed under reduced pressure
  3. customto afford a dark residue
  4. customThe solvent was evaporated
  5. customto afford a plug

Sources & evidence

ORD record
ord-d509d3db14744994aa41aa238ab32200
Source dataset
uspto-grants-2015_02
Patent number
US08946239B2

Reaction notes

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