Phosphorus oxychloride → HCID 59312360, compound

HRID 2077053Notes

Reaction equation

HRID 2077053 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([N:13]1[CH2:19][CH2:18][C:17]2[C:20](=O)[NH:21][C:22]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)=[N:23][C:16]=2[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>[Cl-].C([N+](CC)(CC)CC)C.C(#N)CC>[CH2:6]([N:13]1[CH2:19][CH2:18][C:17]2[C:20]([Cl:3])=[N:21][C:22]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)=[N:23][C:16]=2[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136058092HCID 136058092, compound

Product 1

HCID 59312360HCID 59312360, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 7854PropionitrileSolvent

Conditions

Temperature
100 °C

Procedure

Phosphoryl chloride (1.33 ml, 14.3 mmol) and tetra-ethyl ammonium chloride (472 mg, 2.85 mmol) were added to a solution of the product of Step A (361 mg, 0.95 mmol) in propionitrile (10 ml) and heated to 100° C. for 17 h. The reaction mixture was concentrated in vacuo then azeotroped with toluene then dichloromethane. The residue was partitioned between dichloromethane (30 ml) and water (20 ml), stirred for 30 min then the organic layer was separated, dried over magnesium sulphate and concentrated in vacuo to give the title compound as a foam in 87.7% yield, 332 mg.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthen azeotroped with toluene
  3. customThe residue was partitioned between dichloromethane (30 ml) and water (20 ml)
  4. customthe organic layer was separated
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e199dbeaa8ed49efb3200f3aec78b74f
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

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