Dichloromethane → N-{3-[3-Benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylideneamino]phenyl}succinamic Acid

HRID 1241990Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]2[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12](=[O:21])[C:11](=[C:22]3[N:26]([CH3:27])[C:25]4[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=4[S:23]3)[S:10]2)[CH:5]=[CH:6][CH:7]=1.C(Cl)Cl.[C:35]1(=[O:41])[O:40][C:38](=[O:39])[CH2:37][CH2:36]1>C(Cl)(Cl)Cl>[CH2:14]([N:13]1[C:12](=[O:21])[C:11](=[C:22]2[N:26]([CH3:27])[C:25]3[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=3[S:23]2)[S:10][C:9]1=[N:8][C:4]1[CH:3]=[C:2]([NH:1][C:35](=[O:41])[CH2:36][CH2:37][C:38]([OH:40])=[O:39])[CH:7]=[CH:6][CH:5]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a 25 mL flask was added 2-(3-aminophenylimino)-3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)thiazolidine-4-one (100 mg, 225 μmol), anhydrous DCM (5 mL) and CHCl3 (3 mL). To the solution was added succinic anhydride (23 mg, 239 μmol). The reaction solution was allowed to stir at 50° C. for 1.5 h. The white precipitates were collected by filtration under reduced pressure, washed with DCM (10 mL) and hexanes (20 mL), and then dried under vacuum to give the title compound (75 mg, 61%). MS(ESI): 545 (MH+).

Workup

customThe white precipitates
filtrationwere collected by filtration under reduced pressure
washwashed with DCM (10 mL) and hexanes (20 mL)
customdried under vacuum

Sources & evidence

ORD record: ord-8dffcda90c22435993afa43212aabac5
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115640B2

Reaction notes

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