Dimethylformamide dimethyl acetal → 2-(2-Bromothiophene-5-carbonyl)-3-(dimethylamino)acrylonitrile

HRID 2267435Notes

Reaction equation

HRID 2267435 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7](=[O:11])[CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[Br:1][C:2]1[S:6][C:5]([C:7]([C:8](=[CH:14][N:15]([CH3:17])[CH3:16])[C:9]#[N:10])=[O:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 112876633-(5-Bromothiophen-2-yl)-3-oxopropanenitrile

Product 1

HCID 543239012-(2-Bromothiophene-5-carbonyl)-3-(dimethylamino)acrylonitrile

Conditions

Temperature
100 °C

Procedure

3-(5-Bromothiophen-2-yl)-3-oxopropanenitrile (4 g, 17 mmol) was treated with dimethyl formamide dimethylacetal and the mixture heated to 100° C. After 1 h, the mixture was allowed to cool down to room temperature. The yellow solid that precipitated was collected by suction filtration and washed well with diethyl ether. Yield=4.6 g. MS (M+H)+ 284.

Workup

  1. temperatureto cool down to room temperature
  2. filtrationThe yellow solid that precipitated was collected by suction filtration
  3. washwashed well with diethyl ether

Sources & evidence

ORD record
ord-ec1d5003758443f987bfc3889ea3699f
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

Loading…