Pyridine → HCID 86699913, compound

HRID 530475Notes

Reaction equation

HRID 530475 reaction equation
[Cl:1][C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1.[C:19]1([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[C:19]1([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:2]([Cl:1])=[O:4])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 615235-Phenyl-1-pentanolHCID 94429Triphosgene

Product 1

HCID 86699913HCID 86699913, compoundYield 188.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

In a four necked round bottom flask, triphosgene (22.0 g, 74.2 mmol) was dissolved in toluene (325 mL) under argon. After cooling at 0° C., pyridine (19.2 mL, 237.5 mmol) was added dropwise during 1 h and the resulting suspension stirred for 1 h at 0° C. 5-phenylpentanol (25 mL, 148.4 mmol) was added drop wise in 30 min. After stirring at rt for 16 h the solid was filtered-off and the solvent removed under vacuum yielding the title compound (31.7 g, 94%), which was used in the next step without further purification. Rf=0.75 (Cy/AcOEt 8:2). FTIR (cm−1): 3087, 3063, 3027, 2936, 2859, 1778, 1744, 1604, 1496, 1455, 1382, 1260, 1146, 1031, 941, 835, 731, 696.

Workup

  1. stirringAfter stirring at rt for 16 h the solid
  2. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-f7c9c12d545c41e597d82c173a1198be
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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