Hydrochloric Acid → HCID 20159861, compound
Reaction equation
CO[CH:3]=[C:4]([CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11])[CH:5]=O.Cl.[CH2:13]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[NH:23])=[CH:20][CH:19]=1)[CH2:14][CH2:15][CH2:16][CH3:17].C[O-].[Na+].[Na].Cl>CO>[CH2:7]([C:4]1[CH:5]=[N:23][C:22]([C:21]2[CH:25]=[CH:26][C:18]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:19][CH:20]=2)=[N:24][CH:3]=1)[CH2:8][CH2:9][CH:10]=[CH2:11]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of 2.4 g of 3-methoxy-2-(4-pentenyl)acrolein and 3.4 g of p-pentylbenzamidine hydrochloride in 30 ml of methanol was treated dropwise while stirring with a sodium methylate solution prepared from 0.55 g of sodium and 5 ml of methanol. The reaction mixture was stirred overnight at 50° C. and then neutralized (pH 5) with 3N hydrochloric acid. The solvent was distilled off and the residue was taken up in diethyl ether and water. The aqueous phase was back-extracted with diethyl ether. The organic phase was phase was washed with water, dried over sodium sulphate and concentrated. Chromatographic separation of the residue on silica gel with hexane/ethyl acetate gave 5-(4-pentenyl)-2-(p-pentylphenyl)pyrimidine as a colourless liquid; m.p. (C-I) 8.0° C., cl.p. (N-I) -4.5° C.
Workup
- distillationThe solvent was distilled off
- extractionThe aqueous phase was back-extracted with diethyl ether
- washwas washed with water
- dry with materialdried over sodium sulphate
- concentrationconcentrated
- customChromatographic separation of the residue on silica gel with hexane/ethyl acetate
Sources & evidence
- ORD record
- ord-357303d33a504da98a8ab08bed3bb0d3
- Source dataset
- uspto-grants-1987_11
- Patent number
- US04709030
Reaction notes
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