Phosphorus oxychloride → HCID 57958802, compound

HRID 1774116Notes

Reaction equation

HRID 1774116 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]=[CH:13][N:12]=[C:11]3O)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.O=P(Cl)(Cl)[Cl:30]>C1(C)C=CC=CC=1>[Cl:30][C:11]1[C:10]2[C:15](=[CH:16][CH:17]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:9]=2)[N:14]=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178517960HCID 178517960, compound

Product 1

HCID 57958802HCID 57958802, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of the product of example 7 (720 mg, 3 mmol) in toluene (20 ml) was added diisopropylethylamine (1.5 ml, 9 mmol) and POCl3 (0.84 ml, 9 mmol). The mixture was refluxed for 1 hour. The solvents were evaporated in vacuo. The residue was redissolved in dichloromethane and the organic layer was washed with ice water till pH 6-7. The combined organic layers were dried over MgSO4 and concentrated to yield the title compound as a yellow solid (700 mg, yield: 90%) which was characterized by its mass spectrum as follows: MS (m/z): 259 ([M+H]+, 100).

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customThe solvents were evaporated in vacuo
  3. dissolutionThe residue was redissolved in dichloromethane
  4. washthe organic layer was washed with ice water till pH 6-7
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a190982ae4c54f918ca67911c4a7c7f0
Source dataset
uspto-grants-2016_02
Patent number
US09259426B2

Reaction notes

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