Phenylacetonitrile → HCID 22599823, compound

HRID 1759968Notes

Reaction equation

HRID 1759968 reaction equation
CC(C)([O-])C.[K+].[C:7]1([CH2:13][C:14]#[N:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[C:17]1[CH:22]=[C:21]([S:23][CH3:24])[N:20]=[CH:19][N:18]=1.[Cl-].[NH4+]>O1CCCC1>[C:14]([CH:13]([C:17]1[CH:22]=[C:21]([S:23][CH3:24])[N:20]=[CH:19][N:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:15]

Participants

6

Reactant 4

HCID 8794PhenylacetonitrileHCID 25517Ammonium ChlorideHCID 218130774-Chloro-6-(methylsulfanyl)pyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 22599823HCID 22599823, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In 30 ml of tetrahydrofuran was suspended 5.24 g of potassium t-butoxide, to which 2.63 g of phenylacetonitrile and 3.0 g of 4-chloro-6-methylthiopyrimidine, followed by stirring at 0° C. for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with ethyl acetate. The organic layers were combined and washed with a saturated aqueous sodium chloride solution, and the combined organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 3.67 g of 4-(α-cyanobenzyl)-6-methylthiopyrimidine.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed with a saturated aqueous sodium chloride solution
  3. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9ee5b8655b7d47af9a80ad045076640d
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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