Chloroform → HCID 57625947, compound

HRID 1875495Notes

Reaction equation

HRID 1875495 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=O)[C:5]2[C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=3[O:8][C:6]=2[N:7]=1.O=P(Cl)(Cl)[Cl:18].C(Cl)(Cl)Cl.CCCCCC>C(OC(=O)C)(=O)C>[Cl:18][C:4]1[C:5]2[C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=3[O:8][C:6]=2[N:7]=[C:2]([CH3:1])[N:3]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8058HexaneHCID 24813Phosphorus oxychlorideHCID 57625950HCID 57625950, compound

Product 1

HCID 57625947HCID 57625947, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a 50 mL flask was added 3 (2.04 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 1.67 g (82%) of 4 as a yellow solid: TLC Rf 0.41 (Hexane/EtOAc 15:1); mp 42.4-43.8° C.; 1H NMR (DMSO-d6) δ 1.79 (q, 2H, J=8 Hz), 1.87 (q, 2H, J=8 Hz), 2.63 (s, 3H), 2.75 (d, 4H, J=8 Hz).

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-10f89351c9d7467d86b6c1cd38353752
Source dataset
uspto-grants-2012_11
Patent number
US08309564B2

Reaction notes

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