Dimethylformamide → HCID 22597170, compound

HRID 1861220Notes

Reaction equation

Br[C:2]1[C:3]([O:20][CH:21]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:22][CH:23]([CH3:25])[CH3:24])=[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+].[NH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[SH:43].CN(C=O)C>O>[NH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[S:43][C:2]1[C:3]([O:20][CH:21]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:22][CH:23]([CH3:25])[CH3:24])=[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 500 ml three neck round bottom flask was equipped with a mechanical stirrer, heating mantle and condenser. To the flask was added 52.5 g (0.11 mole) of 3-bromo-2-(1-isobutyl-3-methylbutoxy)-7H-benzo[de]anthracene-7-one (4), 9.2 g (0.087 mole) sodium carbonate, 16.0 g (0.13 mole) 2-aminothiophenol and 170 g DMF. The mixture was agitated well and heated at 120-130° C. for three hours. The reaction was cooled to 25° C. and 300 g water was added. The reaction mixture was extracted twice with 250 g chloroform. The organic layers were combined and washed twice with 250 g water. The solvent was removed on a rotary evaporator. The yield of crude product was 55 g of a dark brown oil which was used as such in the next step.

Workup

temperatureheating mantle and condenser
temperatureThe reaction was cooled to 25° C.
extractionThe reaction mixture was extracted twice with 250 g chloroform
washwashed twice with 250 g water
customThe solvent was removed on a rotary evaporator

Sources & evidence

ORD record: ord-ba8da0f1fdd1480898a7cbe595237636
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531613B1

Reaction notes

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