Phosphorus oxychloride → HCID 10309275, compound

HRID 916971Notes

Reaction equation

HRID 916971 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:14][C:13](=O)[C:12]([C:16]#[N:17])=[CH:11][C:10]=1[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:13]1[N:14]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[C:10]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[CH:11][C:12]=1[C:16]#[N:17]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 69417510HCID 69417510, compound

Product 1

HCID 10309275HCID 10309275, compound

Procedure

To an oven-dried round bottom flask fitted with a condenser was added the product of Step C (0.350 g; 0.986 mmol) and excess phosphorous oxychloride (1 mL). The reaction mixture was heated to reflux for 16 hours. The reaction mixture was allowed to cool to room temperature, and the volatiles were removed in vacuo. The residue was dissolved in ethyl acetate and washed with saturated NaHCO3 solution (2×), water, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification was done by MPLC (silica gel; 0-10% ethyl acetate:hexane) to afford 0.283 g of the desired product: m/e=375 (M+2) Rt=4.36 min on LCMS.

Workup

  1. customTo an oven-dried round bottom flask fitted with a condenser
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 16 hours
  4. customthe volatiles were removed in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with saturated NaHCO3 solution (2×), water, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification

Sources & evidence

ORD record
ord-1cd6776f5be94e3cbf28fefccd647eb8
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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