Pyrimidine, 1,2,5,6-tetrahydro-2,2,4,6,6-pentamethyl- → p-Toluenesulfonic acid

HRID 1076999Notes

Reaction equation

HRID 1076999 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:13][C:14]1[CH2:19][C:18]([CH3:21])([CH3:20])[NH:17][C:16]([CH3:23])([CH3:22])[N:15]=1>CC(C)=O>[C:2]1([CH3:12])[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:6][CH:7]=1.[CH3:13][C:14]1[CH2:19][C:18]([CH3:21])([CH3:20])[NH:17][C:16]([CH3:23])([CH3:22])[N:15]=1

Participants

5

Reactant 2

HCID 68396Pyrimidine, 1,2,5,6-tetrahydro-2,2,4,6,6-pentamethyl-HCID 521998p-Toluenesulfonic acid monohydrate

Product 2

HCID 6101p-Toluenesulfonic acidHCID 68396Pyrimidine, 1,2,5,6-tetrahydro-2,2,4,6,6-pentamethyl-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 19 g. of p-toluenesulfonic acid monohydrate in 40 ml. of acetone was added dropwise to a solution of 15.5 g. of acetonine in 30 ml. of acetone under cooling to 0°-5°C. and under stirring, to form p-toluenesulfonic acid salt of acetonine. The mixture was stirred at 25°C. for 10 hours to effect the reaction and cooled with ice. Crystals thus formed were filtered out and washed with cold acetone and the washing was combined with the filtrate and concentrated. The concentration residue was extracted with benzene. The benzene solution was washed with 20% aqueous sodium hydrogencarbonate solution and dried with anhydrous potassium carbonate. Benzene was then distilled out. The residue was subjected to distillation under reduced pressure to obtain 13.5 g. of triacetonamine in the form of pale yellow liquid boiling at 79°C./6 mmHg. Yield, 86.7%.

Sources & evidence

ORD record
ord-eb102ee6265d482c8fa17d0092821f59
Source dataset
uspto-grants-1976_05
Patent number
US03959298

Reaction notes

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