Acetophenone → 1-[3-Chloro-2-(5-chloro-benzothiazol-2-ylsulfanyl)-5-nitro-phenyl]-ethanone

HRID 1865521Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([SH:10])=[N:7][C:6]=2[CH:11]=1.[H-].[Na+].Cl[C:15]1[C:20]([Cl:21])=[CH:19][C:18]([N+:22]([O-:24])=[O:23])=[CH:17][C:16]=1[C:25](=[O:27])[CH3:26].C(C1C=CC=CC=1)(=O)C>CN(C=O)C>[Cl:21][C:20]1[C:15]([S:10][C:8]2[S:9][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:11][C:6]=3[N:7]=2)=[C:16]([C:25](=[O:27])[CH3:26])[CH:17]=[C:18]([N+:22]([O-:24])=[O:23])[CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a 0.55M solution of 5-chloro-2-mercaptobenzothiazole, obtained from Aldrich, (5.55 g, 27.5 mmol) in DMF at ambient temperature was added NaH, 60% oil dispersion obtained from Aldrich, (1.2 g, 30.0 mmol) portionwise followed by 1-(2,3-Dichloro-5-nitro-phenyl)-ethanone (248) (5.83 g, 25 mmol). The reaction solution turned from bright orange to deep red upon acetophenone addition and was heated to 60° C. for 1 hour. The mixture was allowed to cool for a couple of minutes and the product was precipitated out of solution by the slow addition of H2O (250 mL). After 1 h of stirring the product was collect by vacuum filtration using a buchner funnel, dried under a stream of air for 3 h, and triterated with a 1:1 MeOH/CH2Cl2 solution (200 mL) to yield 5.2 g (52%) of 251 as an orange solid. An additional 3.77 g (39%) could be isolated by purifying the mother liquor using column chromatography (dry load, 100% CH2Cl2).

Workup

temperatureto cool for a couple of minutes
customthe product was precipitated out of solution by the slow addition of H2O (250 mL)
filtrationwas collect by vacuum filtration
customdried under a stream of air for 3 h

Sources & evidence

ORD record: ord-dd13a12a9c644861aa18dd2b8a244d21
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07626033B2

Reaction notes

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