Dimethylformamide → 3-[(2-Aminophenyl)thio]-2-[(2-ethylhexyl)oxy]-7h benzo[de]anthracene-7-one

HRID 1861217Notes

Reaction equation

Br[C:2]1[C:3]([O:20][CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26])=[CH:4][C:5]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12](=[O:19])[C:11]3[C:6]=2[C:7]=1[CH:8]=[CH:9][CH:10]=3.C(=O)([O-])[O-].[Na+].[Na+].[NH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[SH:42].CN(C=O)C>O>[NH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[S:42][C:2]1[C:3]([O:20][CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26])=[CH:4][C:5]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12](=[O:19])[C:11]3[C:6]=2[C:7]=1[CH:8]=[CH:9][CH:10]=3

Participants

Conditions

Temperature: 125 °C

Procedure

A 250 ml three neck round bottom flask was equipped with a mechanical stirrer, heating mantle and condenser. To the flask was added 27 g of 3-bromo-2-[(2-ethylhexyl)oxy]-7H-benzo[de]anthracene-7-one, 5.0 g sodium carbonate, 8.5 g 2-aminothiophenol and 80 g DMF. The mixture was agitated well, heated to 120-130° C., and held at 120-130° C. for three hours. Sodium carbonate (1.0 g) and 1.2 g 2-aminothiophenol were added and the mixture heated for an additional one hour. The reaction mixture was cooled to 25° C. and 250 g of water were added. The reaction mixture was extracted twice with 200 g chloroform. The organic layers were combined and washed twice with 250 g water. The solvent was removed on a rotary evaporator, then the crude product was passed through a flash silica gel column using methylene chloride as the elutant. The product fractions were collected and the solvent removed using a rotary evaporator. The yield of semi-solid 3-[(2-aminophenyl)thio]-2-[(2-ethylhexyl)oxy]-7H-benzo[de]anthracene-7-one was 27.5 g.

Workup

temperatureheating mantle and condenser
temperaturethe mixture heated for an additional one hour
temperatureThe reaction mixture was cooled to 25° C.
extractionThe reaction mixture was extracted twice with 200 g chloroform
washwashed twice with 250 g water
customThe solvent was removed on a rotary evaporator
customThe product fractions were collected
customthe solvent removed
customa rotary evaporator

Sources & evidence

ORD record: ord-dcc70151d2f0408c8f73562dca089118
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531613B1

Reaction notes

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