(Methylsulfonyl)acetonitrile → HCID 67639908, compound

HRID 1586633Notes

Reaction equation

HRID 1586633 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[O:13][CH3:14].[CH3:15][S:16]([CH2:19][C:20]#[N:21])(=[O:18])=[O:17]>N1CCCCC1.C(O)C>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[C:19]([S:16]([CH3:15])(=[O:18])=[O:17])[C:20]#[N:21])=[CH:7][C:6]=1[O:13][CH3:14]

Participants

5

Reactant 2

HCID 75283(Methylsulfonyl)acetonitrileHCID 31527124-(2-hydroxyethoxy)-3-methoxybenzaldehyde

Product 1

HCID 67639908HCID 67639908, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(2-hydroxyethoxy)-3-methoxybenzaldehyde (0.98 g, 0.005 mol), (see Example 1 of U.S. Pat. No. 4,707,537, supra), methylsulfonylacetonitrile (0.60 g, 0.005 m), ethanol (10 mL) and piperidine (5 drops) is heated at reflux for 1 hour, during which time the product crystallizes. The reaction mixture is allowed to cool and the very pale yellow product is collected by filtration, washed with ethanol and dried in air. The yield of product is 1.05 g (70.9%). Mass spectrometry supports the following structure: ##STR22## In methylene chloride the product has an absorption maximum at 362 nm.

Workup

  1. temperatureat reflux for 1 hour, during which time the product
  2. customcrystallizes
  3. temperatureto cool
  4. filtrationthe very pale yellow product is collected by filtration
  5. washwashed with ethanol
  6. customdried in air

Sources & evidence

ORD record
ord-ada37b2f74a24a89a75c5cc1e926bff0
Source dataset
uspto-grants-1993_06
Patent number
US05215876

Reaction notes

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