Methanol → 1,5-Bis(mesitylamino)-3,7-bis(phenylmercapto)-anthraquinone

HRID 1372796Notes

Reaction equation

[C:1]1([CH3:38])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[C:23]2[C:22](=[O:24])[C:21]3[C:16](=[C:17]([NH:26][C:27]4[C:32]([CH3:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:28]=4[CH3:35])[CH:18]=[C:19](Br)[CH:20]=3)[C:15](=[O:36])[C:14]=2[CH:13]=[C:12](Br)[CH:11]=1.[C:39]1([S-:45])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[Na+].CO>CN(C=O)C>[C:1]1([CH3:38])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[C:23]2[C:22](=[O:24])[C:21]3[C:16](=[C:17]([NH:26][C:27]4[C:32]([CH3:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:28]=4[CH3:35])[CH:18]=[C:19]([S:45][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH:20]=3)[C:15](=[O:36])[C:14]=2[CH:13]=[C:12]([S:45][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:11]=1

Participants

Conditions

Temperature: 120 °C

Procedure

16.5 g of 1,5-bis(mesitylamino)-3,7-dibromoanthraquinone are suspended at RT in 50 ml of DMF and heated to 120° C. After cooling to 50° C., a suspension of 8.5 g of sodium thiophenolate in 25 ml of DMF is added thereto. The mixture is then heated to 120° C. again and stirred at that temperature for 1.5 hours. After cooling the mixture to 60° C., 100 ml of methanol are added and the mixture is stirred overnight at RT. The precipitate is filtered off, washed with a methanol/water mixture (1:1) and dried in vacuo.

Workup

temperatureAfter cooling to 50° C.
additionis added
temperatureThe mixture is then heated to 120° C. again
temperatureAfter cooling the mixture to 60° C.
stirringthe mixture is stirred overnight at RT
filtrationThe precipitate is filtered off
washwashed with a methanol/water mixture (1:1)
customdried in vacuo

Sources & evidence

ORD record: ord-4036e7137c384ab58c6e787b8a9a30f5
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07160335B2

Reaction notes

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