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Pyridine → HCID 49787365, compound

HRID 1518600
Notes
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Reaction equation

HRID 1518600 reaction equation
[CH3:1][CH:2]1[CH:7]([CH3:8])[CH2:6][CH2:5][CH:4]([CH3:9])[CH:3]1[OH:10].[N:11]1[CH:16]=[CH:15]C=[CH:13][CH:12]=1.Cl[C:18](Cl)([O:20]C(=O)OC(Cl)(Cl)Cl)Cl.C(NCC)C>ClCCl>[CH3:1][CH:2]1[CH:7]([CH3:8])[CH2:6][CH2:5][CH:4]([CH3:9])[CH:3]1[O:10][C:18](=[O:20])[N:11]([CH2:12][CH3:13])[CH2:16][CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 8021DiethylamineHCID 94429TriphosgeneHCID 202697172,3,6-Trimethylcyclohexanol

Product 1

HCID 49787365HCID 49787365, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
3×

Conditions

Temperature
0 °C

Procedure

4.27 g (30 mmol) of 2,3,6-trimethylcyclohexanol were placed with 110 ml dichlormethane in a 250 ml vessel at room temperature and 3.08 g (39 mmol) of pyridine were added. The reaction mixture was cooled to 0° C. and 3.56 g (12 mmol) of triphosgene in 15 ml dichlormethane were added dropwise. After five minutes 2.37 g (30 mmol) pyridine were added. Subsequently, 2.19 g (30 mmol) of diethylamine in 15 ml dichlormethane were added dropwise, the resulting mixture was allowed to come to ambient temperature and then quenched with water. After separation of the phases, the water phase was extracted once with dichlormethane and the combined organic phases were concentrated. The raw product was purified by distillation and column chromatography to yield 1.5 g of the desired product as a mixture of isomers with a purity of 99.4%.

Workup

  1. customto come to ambient temperature
  2. customquenched with water
  3. customAfter separation of the phases
  4. extractionthe water phase was extracted once with dichlormethane
  5. concentrationthe combined organic phases were concentrated
  6. distillationThe raw product was purified by distillation and column chromatography

Sources & evidence

ORD record
ord-a51f7b88efa945389ef2ed4bcecd4c88
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09072676B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes