N,N,N',N'-Tetramethylethylenediamine → HCID 19930263, compound

HRID 22431Notes

Reaction equation

C([N-]C(C)C)(C)C.[Li+].[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[N:18])[C:12]=1[CH3:19])#[N:10].CN(C)CCN(C)C.[C:28]1([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]I)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCCC1.O>[C:28]1([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:19][C:12]2[C:13]([C:17]#[N:18])=[CH:14][CH:15]=[CH:16][C:11]=2[C:9]#[N:10])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of lithium diisopropylamide 1.5M in tetrahydrofuran (6 ml, 9 mmol) was added dropwise to a stirred solution of 2,6-dicyanotoluene (0.85 g, 6 mmol) and tetramethyl ethylenediamine (1.04 g, 9 mmol) in dry tetrahydrofuran (50 ml), cooled to -70° C. under nitrogen. After one hour, 8-phenyloctyl iodide (2.15 g, 6.8 mmol) was added dropwise at -70° C. to the intense blue suspension, then allowed to warm to 0° C. over one hour. Water (100 ml) was added (cautiously at first) to the brown mixture and then extracted with diethyl ether (50 ml). The extracts were washed with 2M hydrochloric acid, dried, filtered and evaporated to a brown oil (2.67 g). Purified by chromatography on flash silica eluting with dichloromethane gave 2-(9-phenylnonyl)-1,3-benzenedicarbonitrile as an oil.

Workup

temperatureto warm to 0° C. over one hour
extractionextracted with diethyl ether (50 ml)
washThe extracts were washed with 2M hydrochloric acid
customdried
filtrationfiltered
customevaporated to a brown oil (2.67 g)
customPurified by chromatography on flash silica eluting with dichloromethane

Sources & evidence

ORD record: ord-dac3f5e3981d43a491e71e12d30ff55a
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05428065

Reaction notes

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