Sodium Carbonate → HCID 19350310, compound
Reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([NH:13][CH2:14][CH:15]=[CH2:16])[CH:11]=[CH2:12].C(=O)([O-])[O-].[Na+].[Na+].CN(C)P(N(C)C)(N(C)C)=O>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C=CC(O)=CC=1)O.O>[CH2:10]([N:13]([CH2:14][CH:15]=[CH2:16])[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH:11]=[CH2:12]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 110 °C
Procedure
A mixture of 25.0 g (0.10 mol) of 4-fluorobenzaldeyde, 19.6 g (0.20 mol) of diallylamine, 21.3 g (0.20 mol) of sodium carbonate, 150 mL of hexamethylphosphoramide (HMPA), 0.20 g of hydroquinone, and 4 drops of tricaprylmethylammonium chloride was heated under nitrogen with stirring at 110° C. for 113 hr. The reaction mixture was cooled and poured into 1.5 L of water, and the resulting solution was extracted with toluene (4×300 mL). The combined extracts were washed with water (3×250 mL), dried (MgSO4), and the solvent was removed at reduced pressure. The brown residue was fractionally distilled in vacuo to provide 22.3 g (55%) of a pale yellow oil, bp 128°-142° C. (0.16 mm).
Workup
- temperaturewas heated under nitrogen
- temperatureThe reaction mixture was cooled
- extractionthe resulting solution was extracted with toluene (4×300 mL)
- washThe combined extracts were washed with water (3×250 mL)
- dry with materialdried (MgSO4)
- customthe solvent was removed at reduced pressure
- distillationThe brown residue was fractionally distilled in vacuo
Sources & evidence
- ORD record
- ord-99eb2d0d31d240a4b4cf06458625b140
- Source dataset
- uspto-grants-1988_12
- Patent number
- US04792208
Reaction notes
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