Dimethylformamide dimethyl acetal → HCID 54520283, compound

HRID 1602770Notes

Reaction equation

HRID 1602770 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]2[S:10][CH2:9][CH2:8][C:7](=[O:11])[C:6]=2[C:12]=1[CH3:13].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>>[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]2[S:10][CH2:9][C:8](=[CH:17][N:18]([CH3:20])[CH3:19])[C:7](=[O:11])[C:6]=2[C:12]=1[CH3:13]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 152784955,8-Dimethyl-6-bromothiochroman-4-one

Product 1

HCID 54520283HCID 54520283, compound

Procedure

20.0 g (0.074 mole) of the title compound of Step C and 100 mL of N,N-dimethylformamide dimethyl acetal (purchased from Aldrich Chemical Company) were stirred under nitrogen at reflux overnight. The mixture was concentrated, the residue was stirred in water, and filtered. The solid was dissolved in methylene chloride, dried (MgSO4), filtered, and evaporated to dryness to yield 21.54 g of the title compound of Step D as an oil. 1H NMR (CDCl3): δ2.49 (s,3H), 2.56 (s,3H), 3.16 (s,6H), 3.86 (s,2H), 7.34 (s,1H), 7.57 (s,1H).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe mixture was concentrated
  3. filtrationfiltered
  4. dissolutionThe solid was dissolved in methylene chloride
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-2bc371ad97f74c85af4a7a5fdbc81cca
Source dataset
uspto-grants-1999_11
Patent number
US05985799

Reaction notes

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