Magnesium orthosilicate → 2-Cyano-3dimethylamino-1-thien-3-ylpropen-1-one

HRID 1029805Notes

Reaction equation

HRID 1029805 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[O:10][N:9]=[CH:8][CH:7]=2)=[CH:2]1.CO[CH:13](OC)[N:14]([CH3:16])[CH3:15].[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2]>C(Cl)Cl>[CH3:16][N:14]([CH:13]=[C:7]([C:6](=[O:10])[C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)[C:8]#[N:9])[CH3:15]

Participants

5

Reactant 3

HCID 66225Magnesium orthosilicateHCID 78373Dimethylformamide dimethyl acetalHCID 185168865-(Thiophen-3-yl)isoxazole

Product 1

HCID 299434852-Cyano-3dimethylamino-1-thien-3-ylpropen-1-oneYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 41.2 g of 5-(3-thienyl)isoxazole and 36.0 g of dimethylformamide dimethylacetal, under nitrogen, is heated on a steam bath for 4 hours. The reaction is concentrated in vacuo to give a viscous oil which solidified. The residue is dissolved in methylene chloride and passed thru a short column of hydrous magnesium silicate. On cooling, 31.76 g of the desired product is obtained, mp 118°-119°, CI-MS:m/z 206(M+). Concentrating in vacuo the methylene chloride gives an additional 20.2 g of product. (Total recovered 51.96 g, 92%).

Workup

  1. temperatureunder nitrogen, is heated on a steam bath for 4 hours
  2. concentrationThe reaction is concentrated in vacuo
  3. customto give a viscous oil which
  4. temperatureOn cooling

Sources & evidence

ORD record
ord-0d9eff2363a64a55ae09ae964926df0f
Source dataset
uspto-grants-1992_04
Patent number
US05103015

Reaction notes

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