Sodium hydride → HCID 53792436, compound

HRID 359574Notes

Reaction equation

HRID 359574 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]([CH2:18][CH2:19][O:20][C:21](=[O:23])[CH3:22])[C:8]1[CH:17]=[CH:16][C:11]([CH:12]=[CH:13][CH:14]=O)=[CH:10][CH:9]=1)(=[O:3])[CH3:2].P(=O)([O-])O[C:26](CC)(CC)[C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1.[H-].[Na+].[N+](C1C=CC(C=CC=C)=CC=1)([O-])=O>CN(C)C=O.C(O)(=O)C.O.ClCCl>[C:1]([O:4][CH2:5][CH2:6][N:7]([CH2:18][CH2:19][O:20][C:21](=[O:23])[CH3:22])[C:8]1[CH:17]=[CH:16][C:11]([CH:12]=[CH:13][CH:14]=[CH:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Participants

9

Reactant 4

HCID 24758Sodium hydrideHCID 4547414Benzene, 1-(1,3-butadienyl)-4-nitro-HCID 54116589HCID 54116589, compoundHCID 178447636HCID 178447636, compound

Product 1

HCID 53792436HCID 53792436, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the crude reaction product of the previous step, viz. about 5 g of 4-di(2-acetoxyethyl)amino cinnamaldehyde in 125 ml of dimethyl formamide (DMF) were added 6 g of diethyl-4-nitro-benzyl phosphonate, prepared as prescribed by D. H. Wadsworth et al. in the Journal of Organic Chemistry, Vol. 30 (1965), p. 680 ff and, in small successive portions, 1.2 g of sodium hydride in the form of a 60%-dispersion in mineral oil, supplied by Jansses Chimica of Beerse, Belgium. The reaction mixture was stirred for 1 hour at room temperature and then poured, with vigorous stirring at 0° C., into a mixture of 400 ml of dichloromethane, 200 ml of water, and 20 ml of acetic acid. The organic layer was separated, washed twice with a saturated solution of sodium chloride, dried on magnesium sulphate, and concentrated by evaporation to a small volume. The residue was dissolved in 125 ml of dimethyl formamide (DMF), to which was added a solution of 8 g of sodium hydroxide in 25 ml of water. The resulting clear solution was boiled for 30 minutes with refluxing and then poured, with vigorous stirring, into 500 ml of water. The resulting precipitate was filtered off and after-washed with water until the filtrate had a pH of 7. The crude product after drying was crystallized from a mixture of 25 ml of dimethyl formamide (DMF) and 75 ml of dichloromethane. Obtained were 4.0 g of pure 1-(4-di-hydroxyethyl)aminophenyl)-4-(4-nitrophenyl)-1,3 butadiene having a melting point of 195°-198° C.

Workup

  1. customTo a solution of the crude reaction product of the previous step, viz
  2. customprepared
  3. additionpoured
  4. customThe organic layer was separated
  5. washwashed twice with a saturated solution of sodium chloride
  6. customdried on magnesium sulphate
  7. concentrationconcentrated by evaporation to a small volume
  8. dissolutionThe residue was dissolved in 125 ml of dimethyl formamide (DMF), to which
  9. additionwas added a solution of 8 g of sodium hydroxide in 25 ml of water
  10. waitThe resulting clear solution was boiled for 30 minutes
  11. temperaturewith refluxing
  12. additionpoured, with vigorous stirring, into 500 ml of water
  13. filtrationThe resulting precipitate was filtered off
  14. washafter-washed with water until the filtrate
  15. dry with materialThe crude product after drying
  16. customwas crystallized from a mixture of 25 ml of dimethyl formamide (DMF) and 75 ml of dichloromethane
  17. customObtained

Sources & evidence

ORD record
ord-7d72d224e8bc4794aafa638e7c897668
Source dataset
uspto-grants-1991_03
Patent number
US05001209

Reaction notes

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