Acetonitrile → HCID 20505011, compound

HRID 1701993Notes

Reaction equation

HRID 1701993 reaction equation
Cl.[CH3:2][NH:3][C:4](=[NH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl[CH2:13][C:14](=O)[CH2:15][C:16]([OH:18])=[O:17].C[Si](C)(C)N[Si](C)(C)C.C[Si](C)(C)Cl.[C:34](#N)[CH3:35]>>[CH3:2][N:3]1[CH:13]=[C:14]([CH2:15][C:16]([O:18][CH2:34][CH3:35])=[O:17])[N:11]=[C:4]1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 13838HexamethyldisilazaneHCID 119720Butanoic acid, 4-chloro-3-oxo-HCID 178484899HCID 178484899, compound

Product 1

HCID 20505011HCID 20505011, compound

Procedure

A mixture of 6.12 g of N-methylbenzamidine hydrochloride, 4.95 g of the ethyl ester of 4-chloroacetoacetic acid, 18.5 ml of hexamethyldisilazane, 1.27 ml of trimethylchlorosilane, and 350 ml of acetonitrile was heated under reflux until the analytical TLC control no longer indicated any starting compound (about 72 hours). Then the mixture was allowed to cool, the volume of the reaction solution was reduced, by concentration under vacuum, to about one-half, thereafter combined with 200 ml of water, and repeatedly extracted with an ether/hexane (1/1) mixture. The combined organic phases were dried over magnesium sulfate, the solvent was removed under vacuum, and the residue was purified by column chromatography on silica gel with pentane/0-100% ethyl acetate as the eluent. Yield: 3.53 g (48%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux until the analytical TLC control
  3. customany starting compound (about 72 hours)
  4. temperatureto cool
  5. concentrationthe volume of the reaction solution was reduced, by concentration under vacuum, to about one-half
  6. extractionrepeatedly extracted with an ether/hexane (1/1) mixture
  7. dry with materialThe combined organic phases were dried over magnesium sulfate
  8. customthe solvent was removed under vacuum
  9. customthe residue was purified by column chromatography on silica gel with pentane/0-100% ethyl acetate as the eluent

Sources & evidence

ORD record
ord-1980d30f54794ece8c27bad2666499db
Source dataset
uspto-grants-1983_04
Patent number
US04379927

Reaction notes

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