Thionyl Chloride → 2-[6-(3-[1-Adamantyl]-4-methoxyphenyl)-2-naphthyl]-2-chloro-acetonitrile

HRID 860570Notes

Reaction equation

HRID 860570 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[CH:25]=[C:24]([CH:29](O)[C:30]#[N:31])[CH:23]=[CH:22]5)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O=S(Cl)[Cl:35]>C(Cl)(Cl)Cl.CN(C=O)C>[C:1]12([C:11]3[CH:12]=[C:13]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[CH:25]=[C:24]([CH:29]([Cl:35])[C:30]#[N:31])[CH:23]=[CH:22]5)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 865860482-[6-(3-[1-Adamantyl]-4-methoxyphenyl)-2-naphthyl]-2-hydroxy-acetonitrile

Product 1

HCID 695836662-[6-(3-[1-Adamantyl]-4-methoxyphenyl)-2-naphthyl]-2-chloro-acetonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 2-[6-(3-[1-adamantyl]-4-methoxyphenyl)-2-naphthyl]-2-hydroxy-acetonitrile, (0.314 mg, 0.74 mmol) in anhydrous chloroform (10 mL) were added SOCl2 (0.17 mL, 2.23 mmol) and DMF (3 drops). The reaction mixture was heated under reflux for 40 minutes before it was allowed to cool down, washed with water, saturated NaHCO3, brine to give 2-[6-(3-[1-adamantyl]-4-methoxyphenyl)-2-naphthyl]-2-chloro-acetonitrile that was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 40 minutes before it
  3. temperatureto cool down
  4. washwashed with water, saturated NaHCO3, brine

Sources & evidence

ORD record
ord-8ddf299b0cd947d4b08f2a24c85bf8ea
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

Loading…