1,1-Dimethoxyethyl(dimethyl)amine → HCID 68757576, compound

HRID 1519965Notes

Reaction equation

HRID 1519965 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[C:25](OC)([N:27]([CH3:29])[CH3:28])[CH3:26]>>[CH3:28][N:27]([CH3:29])/[C:25](/[CH3:26])=[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 878351,1-Dimethoxyethyl(dimethyl)amineHCID 68757384HCID 68757384, compound

Product 1

HCID 68757576HCID 68757576, compoundYield 58%

Procedure

A solution of N-(2-acetylthiophen-3-yl)-2-(naphthalen-1-yl)acetamide (197 mg, 0.64 mmol) in N,N-dimethylacetamide dimethyl acetal (0.3 mL, 2.05 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 to give the desired N-(2-(3-(dimethylamino)but-2-enoyl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide (139 mg, 58%) which was used without further purification.

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

Sources & evidence

ORD record
ord-033493b5bea14dcca250fd9fd201ebf4
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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