Benzyltrimethylammonium hydroxide → C8F17CH2CH2Sch2CH(CH3)conhch2CH2CH2N(CH3)2

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Reaction Steps

1,1,2,2-Tetrahydroperfluorodecanethiol (12.04 g, 0.025 mole), N-(3-dimethylaminopropyl)methacrylamide (3.88 g, 0.023 mole), and benzyltrimethylammonium hydroxide in methanol (4 drops) were heated overnight at 70° C. The resultant mixture was stripped of volatiles and distilled at 150°/≠0.1 mm Hg to yield 11.7 g of pale-yellow liquid (78.1% theory) which subsequently crystallized to a solid, m.p. 47°-50° C. NMR showed proton resonances at δ1.05, 3 protons, CH CH3 ; δ1.55, 2 protons, NHCH2CH2CH2N(CH3)2 ; δ2.10, 6 protons, 2 × NCH3 ; δ2.00-δ2.80, 10 protons, CF2CH2CH2SCH2 + NHCH2CH2CH2N; δ3.05; 1 proton, CH(CH3)CO; δ7.50, 1 proton, NH.

Provenance & Evidence