Chloranil → HCID 57913425, compound

HRID 1261742Notes

Reaction equation

[C:1]1([CH:7]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[S:22][C:21]3[CH:20]=[C:19]4[C:10]([S:11][C:12]5[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=5[CH:18]4[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:9][C:8]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>ClC1C=CC=CC=1Cl>[C:1]1([C:7]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[S:22][C:21]3[C:8]=2[CH:9]=[C:10]2[C:19]([CH:20]=3)=[C:18]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[S:11]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 22 °C

Procedure

A mixture of 8.0 g of 7,14-diphenyl-7,14-dihydro-5,12-dithia-pentacene and 3.1 grams of chloranil is heated in 70 ml ortho-dichlorobenzene to 150° C. for one hour. After cooling to 22° C., the product is filtered off and washed with 30 ml of ortho-dichlorobenzene, twice with 15 ml toluene and finally with 30 ml of ethanol. After drying 5.9 g of 7,14-Diphenyl-5,12-dithia-pentacene is obtained as dark violet crystals, mp=320° C. EI-MS: 468 (100%), 436 (7%), 391 (7%), 358 (8%), 234 (11%). The structure is confirmed by single crystal X-ray diffraction analysis: (space group: P-1; cell length: a 5.746(2); b 10.337(2); c 10.623(2); cell angles: α 116.620(11) β 104.914(13) γ 92.354(14)). FIG. 5 shows representations of the product calculated according to the above x-ray data (views other than along crystallographic axes).

Workup

filtrationthe product is filtered off
washwashed with 30 ml of ortho-dichlorobenzene, twice with 15 ml toluene and finally with 30 ml of ethanol
dry with materialAfter drying 5.9 g of 7,14-Diphenyl-5,12-dithia-pentacene
customis obtained as dark violet crystals, mp=320° C

Sources & evidence

ORD record: ord-a4db43e5611b4dc083b9af8dee7d281c
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471019B2

Reaction notes

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