Potassium Carbonate → (E)-4-(2-cyano-3-nitrophenoxy)-N-propylbut-2-enamide

HRID 471676Notes

Reaction equation

HRID 471676 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]([NH:7][CH2:8][CH2:9][CH3:10])=[O:6].[OH:11][C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:13]=1[C:14]#[N:15].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[C:14]([C:13]1[C:16]([N+:20]([O-:22])=[O:21])=[CH:17][CH:18]=[CH:19][C:12]=1[O:11][CH2:2]/[CH:3]=[CH:4]/[C:5]([NH:7][CH2:8][CH2:9][CH3:10])=[O:6])#[N:15]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 125032052-Hydroxy-6-nitrobenzonitrileHCID 86657475(E)-4-Bromo-N-propylbut-2-enamide

Product 1

HCID 66745957(E)-4-(2-cyano-3-nitrophenoxy)-N-propylbut-2-enamideYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(E)-4-Bromo-N-propylbut-2-enamide (Elliott, M.; Farnham, A. W.; Janes, N. F.; Johnson, D. M.; Pulman, D. A. Pesticide Science 1987 18(4) 229) (0.14 g, 0.70 mmol), 2-hydroxy-6-nitrobenzonitrile (0.14 g, 0.88 mmol), potassium carbonate (0.39 g, 2.81 mmol), and 18-crown-6 (0.11 g, 0.42 mmol) were refluxed in acetone (6 mL) for 2 h, and then poured into ice water (45 mL). The resultant precipitate was collected by filtration to give 0.16 g (79%) of the title compound as an off white solid. 1H NMR (400 MHz, DMSO-d6) δ 0.84 (t, J=7.2 Hz, 3H), 1.42 (hex, J=7.2 Hz, 2H), 3.06 (q, J=6.8 Hz, 2H), 5.07 (d, J=2.8 Hz, 2H), 6.16 (d, J=16.0 Hz, 1H), 6.71-6.78 (m, 1H), 7.69 (d, J=8.0 Hz, 1H), 7.88-7.96 (m, 2H), 8.11-8.14 (m, 1H).

Workup

  1. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-7a48a843f59147378666e873724f6ea1
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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