Dimethylformamide dimethyl acetal → HCID 53802097, compound

HRID 1979559Notes

Reaction equation

HRID 1979559 reaction equation
[Cl:1][CH2:2][CH:3]1[CH2:7][O:6][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20](=[O:24])[CH2:21][C:22]#[N:23])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:4]1.CO[CH:27](OC)[N:28]([CH3:30])[CH3:29]>>[Cl:1][CH2:2][CH:3]1[CH2:7][O:6][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20](=[O:24])[C:21](=[CH:27][N:28]([CH3:30])[CH3:29])[C:22]#[N:23])([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:4]1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 13143661HCID 13143661, compound

Product 1

HCID 53802097HCID 53802097, compound

Procedure

A solution of 20 g (0.0585 mol) of the above propanenitrile in 75 ml of N,N-dimethylformamide dimethylacetal was refluxed and stirred for 90 mins, and evaporated to dryness. The oil was triturated with ice water which was decanted, and the residue was partitioned between 150 ml of dichloromethane and 150 ml of water. The organic layer was dried with sodium sulfate, concentrated, and filtered through 150 g of Florisil. The column was eluted with ether which was evaporated, and the resulting oil was crystallized from ethanol to give end product. A sample was recrystallized from dichloromethane/ether to give white prisms, mp 107°-110° C.

Workup

  1. customevaporated to dryness
  2. customThe oil was triturated with ice water which
  3. customwas decanted
  4. customthe residue was partitioned between 150 ml of dichloromethane and 150 ml of water
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated
  7. filtrationfiltered through 150 g of Florisil
  8. washThe column was eluted with ether which
  9. customwas evaporated
  10. customthe resulting oil was crystallized from ethanol
  11. customto give end product
  12. customA sample was recrystallized from dichloromethane/ether
  13. customto give white prisms, mp 107°-110° C.

Sources & evidence

ORD record
ord-482e7a2ced4b4bd3b799c34a8df8e31b
Source dataset
uspto-grants-1984_11
Patent number
US04481142

Reaction notes

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