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

HRID 22431
Notes
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Reaction equation

HRID 22431 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 5883962,6-DicyanotolueneHCID 2724682Lithium diisopropylamideHCID 10947018Benzene, (8-iodooctyl)-

Product 1

HCID 19930263HCID 19930263, compound

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 8028TetrahydrofuranSolvent2×

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

  1. temperatureto warm to 0° C. over one hour
  2. extractionextracted with diethyl ether (50 ml)
  3. washThe extracts were washed with 2M hydrochloric acid
  4. customdried
  5. filtrationfiltered
  6. customevaporated to a brown oil (2.67 g)
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes