Water → 2-[5-[2-(2-Benzyloxy-4-dibutylaminophenyl)vinyl]thiophene-2-yl]-3-cyano-2-butenedinitrile

HRID 85320

Reaction equation

[C:1]([C:3]([C:9]#[N:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6])#N.[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([N:32]([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH2:35][CH3:36])[CH:22]=[CH:23][C:24]=1[CH:25]=[CH:26][C:27]1[S:28]C=[CH:30][CH:31]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O.C(Cl)(Cl)Cl>CN(C)C=O>[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([N:32]([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH2:35][CH3:36])[CH:22]=[CH:23][C:24]=1[CH:25]=[CH:26][C:27]1[S:28][C:1]([C:3](=[C:4]([C:7]#[N:8])[C:5]#[N:6])[C:9]#[N:10])=[CH:30][CH:31]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 40 °C

Procedure

In 3 ml of N,N-dimethylformamide, 0.13 g (1.01 mmol) of tetracyanoethylene was dissolved. With stirring under ice cooling, 0.4 g (0.95 mmol) of [3-benzyloxy-4-[2-(thiophene-2-yl)vinyl]phenyl]dibutyl amine was dissolved in 1 ml of N,N-dimethylformamide and added dropwise. The mixture was stirred for 40 minutes and further stirred with heating at 40° C. overnight. After the reaction mixture was poured into 100 ml of water, extraction with chloroform, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography and washed with ethanol to give 157 mg of a black crystal having a mp of 125-130° C. (yield: 31.7%).

Workup

additionadded dropwise
stirringThe mixture was stirred for 40 minutes
stirringfurther stirred
washwashing with a saturated saline solution
dry with materialdrying over anhydrous sodium sulfate, and concentration
customThe residue was purified by silica gel column chromatography
washwashed with ethanol

Sources & evidence

ORD record: ord-77753e04cf7442b29f50ed8998c89950
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846955B2

Linked notes

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