Reaction equation
[CH:1]1[C:11](=[C:12]([C:15]#[N:16])[C:13]#[N:14])[CH:10]=[CH:9][C:3](=[C:4]([C:7]#[N:8])[C:5]#N)[CH:2]=1.[CH2:17]([N:21]([CH2:30][CH2:31][CH2:32][CH3:33])[C:22]1[CH:27]=[CH:26]C=[C:24]([O:28][CH3:29])[CH:23]=1)[CH2:18][CH2:19][CH3:20]>CN(C)C=O>[C:7]([C:4]([C:5]1[CH:26]=[CH:27][C:22]([N:21]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:30][CH2:31][CH2:32][CH3:33])=[CH:23][C:24]=1[O:28][CH3:29])=[C:3]1[CH:2]=[CH:1][C:11](=[C:12]([C:15]#[N:16])[C:13]#[N:14])[CH:10]=[CH:9]1)#[N:8]Participants
Procedure
In 8 ml of N,N-dimethylformamide, 460 mg (2.25 mmol) of 7,7,8,8-tetracyanoquinodimethane was dissolved. With stirring under ice cooling, 500 mg (2.12 mmol) of dibutyl(3-methoxyphenyl)amine was dissolved in 2 ml of N,N-dimethylformamide and added dropwise. The mixture was stirred for 1.5 hours. After the ice bath was removed, the mixture was further stirred for 3.5 hours. After the reaction mixture was poured into 100 ml of water, extraction with ethyl acetate, 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 chloroform to give 226 mg of an off-white crystal having a mp of 215-238° C. (yield: 25.6%).
Workup
- additionadded dropwise
- stirringThe mixture was stirred for 1.5 hours
- customAfter the ice bath was removed
- stirringthe mixture was further stirred for 3.5 hours
- additionAfter the reaction mixture was poured into 100 ml of water, extraction with ethyl acetate
- 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 chloroform
Sources & evidence
- ORD record
- ord-8d622d8f878347c09f01224d029dd60f
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846955B2
Linked notes
Loading…