Dimethylformamide dimethyl acetal → α-[(Dimethylamino)methylene]-β-oxo-2-thiophenepropanenitrile

HRID 968199Notes

Reaction equation

HRID 968199 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:10][N:9]=[CH:8][CH:7]=1.CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>>[CH3:16][N:14]([CH:13]=[C:7]([C:6](=[O:10])[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:8]#[N:9])[CH3:15]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 120499865-(Thiophen-2-YL)-1,2-oxazole

Product 1

HCID 3743025α-[(Dimethylamino)methylene]-β-oxo-2-thiophenepropanenitrile

Procedure

A mixture of Compound 4 (13.0 g, 86 mmol) and dimethylformamide dimethyl acetal (22.4 g, 188 mmol) was refluxed under nitrogen for 3 hrs. Solid precipitated from the reaction mixture. The reaction mixture was cooled, diluted with dichloromethane and ether (1:10, 200 mL). The solid was collected by filtration, triturated with a solution of dichloromethane and ether (1:20, 100 mL). Compound 5 was obtained as an orange solid (13.5 g, 65.4 mmol, 76%). GC/MS, m/z=206 at tR=13.39 min (100%). LC/MS, [M+H]′=207.

Workup

  1. temperaturewas refluxed under nitrogen for 3 hrs
  2. customSolid precipitated from the reaction mixture
  3. temperatureThe reaction mixture was cooled
  4. additiondiluted with dichloromethane and ether (1:10, 200 mL)
  5. filtrationThe solid was collected by filtration
  6. customtriturated with a solution of dichloromethane and ether (1:20, 100 mL)

Sources & evidence

ORD record
ord-ac713917f0a844fa90ecb314fff7a6f4
Source dataset
uspto-grants-2005_10
Patent number
US06958342B2

Reaction notes

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