Phenanthrene → Anthracene, 9,10-bis(phenylethynyl)-

HRID 2186643Notes

Reaction equation

HRID 2186643 reaction equation
N[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:24]#[C:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:6]3[C:11]([C:12]=2[C:16]#[C:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.C1C2C=CC3C(=CC=CC=3)C=2C=CC=1>C1COCC1.C(N(CC)CC)C>[CH:29]1[CH:28]=[CH:27][C:26]([C:25]#[C:24][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]([C:16]#[C:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:13]3[C:4]=2[CH:3]=[CH:2][CH:15]=[CH:14]3)=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 995PhenanthreneHCID 86198273HCID 86198273, compound

Product 1

HCID 82338Anthracene, 9,10-bis(phenylethynyl)-Yield 39.6%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 120 mg of 2-[4-(carboxybutyl)methylaminophenyl]-3-phenyl-5,6-dihydrothioxene prepared as described above (0.5 mmol) in 5.0 mL of THF was cooled in an ice bath for 30 minutes. 5.0 mL of oxalyl chloride was added to the cooled solution. The reaction mixture was stirred at 4° C. for 3 hours. Oxalyl chloride was evaporated on the rotovap under reduced pressure to give the acid chloride of 2-[4-(carboxybutyl)methylaminophenyl]-3-phenyl-5,6-dihydrothioxene. 2-Amino 9,10-bis-phenylethynyl anthracene (1.0 mmol) in 25 mL of dry THF was added to the residue followed by 2 drops of triethyl amine. The heterogeneous reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was worked up as described for thioxene-phenanthrene. The product, 2-amino-9,10-bis(phenylethynyl)anthracene amide of 2-[4-(carboxybutyl)methylaminophenyl]-3-phenyl-5,6-dihydrothioxene (compound 7 in Table 1) was purified on preparative TLC (CH2Cl2: hexane 9:1) to yield 150 mg of yellow glassy solid.

Workup

  1. customThe product, 2-amino-9,10-bis(phenylethynyl)anthracene amide of 2-[4-(carboxybutyl)methylaminophenyl]-3-phenyl-5,6-dihydrothioxene (compound 7 in Table 1) was purified on preparative TLC (CH2Cl2: hexane 9:1)

Sources & evidence

ORD record
ord-2fbbd2f479a94b5da722c27477e0d62d
Source dataset
uspto-grants-2002_06
Patent number
US06406667B1

Reaction notes

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