Dimethylformamide dimethyl acetal → HCID 68755357, compound

HRID 1519962Notes

Reaction equation

HRID 1519962 reaction equation
[C:1]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[NH:9][C:10](=[O:22])[CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)(=[O:3])[CH3:2].CO[CH:25](OC)[N:26]([CH3:28])[CH3:27]>>[CH3:25][N:26]([CH3:28])/[CH:27]=[CH:2]/[C:1]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[NH:9][C:10](=[O:22])[CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)=[O:3]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 68757384HCID 68757384, compound

Product 1

HCID 68755357HCID 68755357, compoundYield 95.8%

Procedure

A solution of N-(2-acetylthiophen-3-yl)-2-(naphthalen-1-yl)acetamide (165 mg, 0.53 mmol) in N,N-dimethylformamide dimethyl acetal (0.2 mL, 1.50 mmol) was heated at 80° C. for 2 h. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was washed with H2O, dried (sodium sulfate), filtered and concentrated under reduced pressure to give the desired N-(2-(3-(dimethylamino)acryloyl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide (185 mg, 95%) which was used without further purification. Method [4] m/z 387.0 (M+Na); rt=2.199 min.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and H2O
  2. washThe organic layer was washed with H2O
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-31829f768d4948cda74ada178569aa20
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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