3-Bromopropionitrile → HCID 12149574, compound

HRID 1583102Notes

Reaction equation

[SH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:24]2[CH:29]=[CH:28][C:27]([SH:30])=[CH:26][CH:25]=2)=[C:9]([C:17]2[CH:22]=[CH:21][C:20]([SH:23])=[CH:19][CH:18]=2)[C:10]2[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:34][CH2:35][C:36]#[N:37]>C1COCC1>[C:36]([CH2:35][CH2:34][S:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:24]2[CH:25]=[CH:26][C:27]([S:30][CH2:34][CH2:35][C:36]#[N:37])=[CH:28][CH:29]=2)=[C:9]([C:17]2[CH:22]=[CH:21][C:20]([S:23][CH2:34][CH2:35][C:36]#[N:37])=[CH:19][CH:18]=2)[C:10]2[CH:11]=[CH:12][C:13]([S:16][CH2:34][CH2:35][C:36]#[N:37])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1)#[N:37]

Participants

Conditions

Temperature: 85 °C

Procedure

1,1,2,2-tetrakis(4-mercaptophenyl) ethylene (0.5 mmol) made in Example 2 was added to 30 ml of THF, and 160 mg (4.0 mmol) of sodium hydride and 0.35 mL (4.0 mmol) of 3-bromopropionitrile were added with stirring in an ice-cooled bath followed by being refluxed at 85° C. for 24 hours. After solvent was evaporated, ice-cooled water was added to the residue, the mixture was acidified with hydrochloric acid, and then was extracted with dichloromethane. The extract was dehydrated with anhydrous magnesium sulfate. Subsequently, it was subjected to a silica gel column chromatography (φ40 mm, height=50 mm, developing solvent: ethyl acetate: chloroform=1:15), and was recrystallized from chloroform and carbon tetrachloride to afford the target compound.

Workup

additionwere added
temperaturecooled bath
customAfter solvent was evaporated
temperatureice-cooled water
additionwas added to the residue
extractionwas extracted with dichloromethane
customwas recrystallized from chloroform and carbon tetrachloride
customto afford the target compound

Sources & evidence

ORD record: ord-12e56f379e9e4bb8a27a133a04223fc7
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06740782B2

Reaction notes

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