Toluene → 4-(2-Thienylmethyl)-2,2,6,6-tetra-methyl-1-oxa-4-aza-2,6-disilacyclohexane

HRID 27876

Reaction equation

[C:1]1([CH2:6][NH2:7])[S:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[CH2:16][Si:17]([CH3:25])([CH3:24])[O:18][Si:19]([CH2:22]Cl)([CH3:21])[CH3:20].C1(C)C=CC=CC=1>O>[S:5]1[CH:4]=[CH:3][CH:2]=[C:1]1[CH2:6][N:7]1[CH2:20][Si:19]([CH3:22])([CH3:21])[O:18][Si:17]([CH3:25])([CH3:24])[CH2:16]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution containing 22.6 g. (0.2 mole) of 2-thenylamine, 44.4 g. (0.44 mole) of triethylamine and 50.0 g. of acetonitrile dried over molecular sieves there is added 46.2 g. (0.2 mole) of 1,3-bis-chloromethyl-1,1,3,3-tetramethyl-disiloxane. The resulting homogenized solution is allowed to stand for 3 days and then heated in a bath at 90° C. for 36 hours. After cooling the mixture is then equiliberated between toluene and water, the organic phase is then washed with two more portions of water and concentrated to give 61.5 g. of a crude oil. Vacuum distillation through a Vigreux column gives 4-(2-thienylmethyl)-2,2,6,6-tetra-methyl-1-oxa-4-aza-2,6-disilacyclohexane; b.p. 78° to 80° C. at 0.1 to 0.11 mm.

Workup

additionTo a solution containing 22.6 g
dry with materialof acetonitrile dried over molecular sieves there
additionis added 46.2 g
temperatureAfter cooling the mixture
washthe organic phase is then washed with two more portions of water
concentrationconcentrated
customto give 61.5 g
distillationVacuum distillation through a Vigreux column

Sources & evidence

ORD record: ord-daa0191ef4ad4921942a85e01f0b9bb3
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04224317

Linked notes

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