Trichloroacetonitrile → HCID 10945728, compound

HRID 1441167Notes

Reaction equation

HRID 1441167 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C@H:5]([OH:10])[CH2:6][CH2:7][CH2:8][CH:9]=1.[Cl:11][C:12]([Cl:16])([Cl:15])[C:13]#[N:14]>C(OCC)C>[Cl:11][C:12]([Cl:16])([Cl:15])[C:13](=[NH:14])[O:10][C@@H:5]1[CH2:6][CH2:7][CH2:8][CH:9]=[C:4]1[Cl:3]

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 24758Sodium hydrideHCID 10887950HCID 10887950, compound

Product 1

HCID 10945728HCID 10945728, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Combine sodium hydride (0.50 g, 60% in oil, 12 mmol) and diethyl ether (50 mL) and cool to 0° C. Add over 15 minutes a solution of (R)-2-chloro-cyclohex-2-enylalcohol (23.0 g, 160 mmol) in diethyl ether (40 mL). Stir until gas evolution ceases. Add a solution of trichloroacetonitrile (20 mL, 200 mmol) in diethyl ether (30 mL). Stir at 0° C. for 30 minutes and then warm to ambient temperature over 1.5 hours. Evaporate the reaction mixture in vacuo to give the title compound.

Workup

  1. stirringStir at 0° C. for 30 minutes
  2. customEvaporate the reaction mixture in vacuo

Sources & evidence

ORD record
ord-5b5a47ef56f54f0fa4ce1c3ec78c4a50
Source dataset
uspto-grants-1996_03
Patent number
US05502253

Reaction notes

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