Methanol, 1,1-diethoxy-, 1-acetate → HCID 53968462, compound

HRID 1199330Notes

Reaction equation

HRID 1199330 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([CH2:12][C:13]#[N:14])=[O:11])=[CH:8][CH:7]=1)(=[O:4])=[O:3].[CH2:17]([O:19][CH:20](OC(=O)C)OCC)[CH3:18]>C(#N)C>[CH2:17]([O:19][CH:20]=[C:12]([C:10](=[O:11])[C:9]1[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:16][CH:15]=1)[C:13]#[N:14])[CH3:18]

Participants

4

Reactant 2

HCID 84166Methanol, 1,1-diethoxy-, 1-acetateHCID 14646930Methanesulfonamide, N-[4-(2-cyanoacetyl)phenyl]-

Product 1

HCID 53968462HCID 53968462, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a slurry of 4-methylsulfonamidobenzoylacetonitrile (7.0 g) in acetonitrile (70 ml), diethoxymethylacetate (16.2 g) was added and the mixture heated at reflux for 30 minutes. The mixture was cooled to room temperature and filtered. The filtrate was poured into 600 ml diethyl ether, after which 800 ml ligroin P950 was added with rapid stirring. A light yellow oil formed in droplets, which spontaneously crystallized. The crystalline product was collected by filtration, washed with ligroin P950, and dried to yield 7.1 g of 2-(ethoxymethylidene)-2-(4'-methylsulfonamidobenzoyl)-acetonitrile.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 30 minutes
  3. filtrationfiltered
  4. additionThe filtrate was poured into 600 ml diethyl ether
  5. additionafter which 800 ml ligroin P950 was added with rapid stirring
  6. customA light yellow oil formed in droplets, which
  7. customspontaneously crystallized
  8. filtrationThe crystalline product was collected by filtration
  9. washwashed with ligroin P950
  10. customdried

Sources & evidence

ORD record
ord-442adddd456d43dfba04429fa1412f6c
Source dataset
uspto-grants-1990_02
Patent number
US04900653

Reaction notes

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