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

HRID 1790242
Notes
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Reaction equation

HRID 1790242 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11616212Methyl 3-[4-(2-chloroethoxy)phenyl]-2-ethoxypropanoateHCID 1317171596-Benzoylbenzothiazolinone

Product 1

HCID 11584254Methyl 3-{4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]phenyl}-2-ethoxypropanoate

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

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 of Example 1 (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 form methanol and yields the title compound in the form of a solid.

Workup

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

Sources & evidence

ORD record
ord-8813f2ad16624e089fe1a0bc73d73751
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07071221B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes