Dimethylformamide dimethyl acetal → HCID 58873079, compound

HRID 1990095Notes

Reaction equation

HRID 1990095 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]#[N:17])=[C:14]([CH2:18][CH3:19])[S:13][C:12]=2[C:20]([NH2:22])=[O:21])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CO[CH:25]([N:28]([CH3:30])[CH3:29])OC>>[CH3:25][N:28]([CH:30]=[N:22][C:20]([C:12]1[S:13][C:14]([CH2:18][CH3:19])=[C:15]([C:16]#[N:17])[C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][CH:7]=1)=[O:21])[CH3:29]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 58873118HCID 58873118, compound

Product 1

HCID 58873079HCID 58873079, compoundYield 82%

Procedure

Prepare a solution of 3-(4-tert-butyl-phenyl)-4-cyano-5-ethyl-thiophene-2-carboxylic acid amide (270 mg, 0.86 mmol) in 4 mL of dry dimethoxymethyl-dimethyl-amine and heat to reflux under nitrogen. After 1 hour allow 1 mL of solvent to distill out of the reaction, then cool the mixture to room temperature. Dilute the slurry with 10 mL of hexanes, filter off the resulting yellow product and wash with 5 mL hexanes. Vacuum-dry the solid overnight to give 261 mg (82%) of the title compound. MS(ES+, m/e)=368 (M++1).

Workup

  1. temperatureheat
  2. temperatureto reflux under nitrogen
  3. distillation1 mL of solvent to distill out of the reaction
  4. additionDilute the slurry with 10 mL of hexanes
  5. filtrationfilter off the resulting yellow product
  6. washwash with 5 mL hexanes
  7. customVacuum-dry the solid overnight

Sources & evidence

ORD record
ord-0df831c3582c435199e42dcb14889943
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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