Tetrahydrofuran → 1-Morpholino-2-cyano-3-(2',3'-dichlorophenyl)-4-nitro-but-1-ene

HRID 1789227Notes

Reaction equation

HRID 1789227 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]=[CH:10][N+:11]([O-:13])=[O:12].[O:14]1[CH2:19][CH2:18][N:17]([CH:20]=[CH:21][C:22]#[N:23])[CH2:16][CH2:15]1.O1CCCC1>C(Cl)(Cl)Cl>[O:14]1[CH2:19][CH2:18][N:17]([CH:20]=[C:21]([C:22]#[N:23])[CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])[CH2:10][N+:11]([O-:13])=[O:12])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 35036541-(2',3'-Dichlorophenyl)-2-nitroethyleneHCID 542638473-Morpholinoacrylonitrile

Product 1

HCID 543069841-Morpholino-2-cyano-3-(2',3'-dichlorophenyl)-4-nitro-but-1-ene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5.0 g of 1-(2',3'-dichlorophenyl)-2-nitroethylene, 3.18 g of 3-morpholinoacrylonitrile and 30 ml of tetrahydrofuran (abs.) are refluxed for 24 hours, and the reaction solution is subsequently concentrated by evaporation. The resulting residue, dissolved in toluene/ethyl acetate (2:1 V/V), is chromatographed through silica gel, and from the eluate is thus obtained the finished product, m.p. 74°-77° C. IR (CHCl3) in cm-1 ; 2200 (CN), 1630 (C=C), 1560 (NO2). NMR (CDCl3) in ppm: 4.5 (m, 4H); 4.7 (m, 4H); 4.8 (ABX, 3H); 6.60 (s, 1H); 7.2-7.5 (m, 3H).

Workup

  1. concentrationthe reaction solution is subsequently concentrated by evaporation
  2. dissolutionThe resulting residue, dissolved in toluene/ethyl acetate (2:1 V/V)
  3. customis chromatographed through silica gel
  4. customfrom the eluate is thus obtained the finished product, m.p. 74°-77° C

Sources & evidence

ORD record
ord-558e3460c7e744ffa8db86530f4fe9eb
Source dataset
uspto-grants-1987_08
Patent number
US04687861

Reaction notes

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