Potassium Carbonate → Methyl 3-{4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]phenyl}-2-ethoxypropanoate

HRID 1790240Notes

Reaction equation

C(=O)([O-])[O-:2].[K+].[K+].[C:7]([C:15]1[CH:24]=[CH:23][C:18]2[N:19]=[CH:20][S:21](=O)[C:17]=2[CH:16]=1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH:36]([O:41][CH2:42][CH3:43])[C:37]([O:39][CH3:40])=[O:38])=[CH:31][CH:30]=1>CN(C)C=O>[C:7]([C:15]1[CH:24]=[CH:23][C:18]2[N:19]([CH2:26][CH2:27][O:28][C:29]3[CH:34]=[CH:33][C:32]([CH2:35][CH:36]([O:41][CH2:42][CH3:43])[C:37]([O:39][CH3:40])=[O:38])=[CH:31][CH:30]=3)[C:20](=[O:2])[S:21][C:17]=2[CH:16]=1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 20 ml of dimethylformamide add potassium carbonate (0.01044 mol) and then 6-benzoylbenzothiazolinone (0.00453 mol). Heat at 100° C. for 1 hour. Add the compound obtained in Step B (0.00348 mol) and heat at 150° C. for 16 hours. Evaporate off the dimethylformamide. Take up the residue in 50 ml of water and then extract with 50 ml of dichloromethane twice. The organic phase is dried over MgSO4 and then evaporated. The residue is recrystallised from methanol and yields the title compound in the form of a solid.

Workup

temperatureheat at 150° C. for 16 hours
customEvaporate off the dimethylformamide
extractionextract with 50 ml of dichloromethane twice
dry with materialThe organic phase is dried over MgSO4
customevaporated
customThe residue is recrystallised from methanol

Sources & evidence

ORD record: ord-18b711fee87f4c259f9e62bbac53b196
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071221B2

Reaction notes

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