HCID 58153059, compound → (2Z,3E,5Z)-5-(1,1-dioxido-3-oxo-1-benzothiophen-2(3H)-ylidene)-2-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)pent-3-enenitrile

HRID 76815Notes

Reaction equation

HRID 76815 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:12])([CH3:11])[CH:3]1[CH2:13][C:14]#[N:15].CO/[CH:18]=[CH:19]/[CH:20]=[C:21]1\[S:22](=[O:32])(=[O:31])[C:23]2[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=2[C:25]\1=[O:26]>>[O:31]=[S:22]1(=[O:32])[C:23]2[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=2[C:25](=[O:26])/[C:21]/1=[CH:20]/[CH:19]=[CH:18]/[C:13](=[C:3]1/[N:2]([CH3:1])[C:10]2[C:5]([C:4]/1([CH3:12])[CH3:11])=[CH:6][CH:7]=[CH:8][CH:9]=2)/[C:14]#[N:15]

Participants

3

Reactant 2

HCID 58153059HCID 58153059, compoundHCID 67262655HCID 67262655, compound

Product 1

HCID 25156262(2Z,3E,5Z)-5-(1,1-dioxido-3-oxo-1-benzothiophen-2(3H)-ylidene)-2-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)pent-3-enenitrile

Conditions

Temperature
210 °C

Procedure

A mixture of (1,3,3-trimethyl-2,3-dihydro-1H-indol-2-yl)acetonitrile (397 mg, 2.00 mmol) and (2Z)-2-[(2E)-3-methoxyprop-2-en-1-ylidene]-1-benzothiophen-3(2H)-one 1,1-dioxide (501 mg, 2.00 mmol) were placed in a 10-mL one-necked round bottom flask. The flask was heated in an oil bath at 210° C. for 2 hours and then cooled to room temperature. The reaction mixture was extracted with dichloromethane (100 mL). The organic solution was passed through a short silica column, the dichloromethane was evaporated and the pure dye was obtained by recrystallization from methanol. The yield was 511 mg of green crystals (63% of theory).

Workup

  1. customwere placed in a 10-mL one-necked round bottom flask
  2. temperaturecooled to room temperature
  3. extractionThe reaction mixture was extracted with dichloromethane (100 mL)
  4. customthe dichloromethane was evaporated
  5. customthe pure dye was obtained by recrystallization from methanol

Sources & evidence

ORD record
ord-a2b11419ae75457da89693b243276c18
Source dataset
uspto-grants-2014_09
Patent number
US08835632B2

Reaction notes

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