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Potassium Carbonate → 6-(3-Thienylmethoxy)-1,3-benzoxathiol-2-one

HRID 322947
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Reaction equation

HRID 322947 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[S:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]1[CH:24]=[CH:23][S:22][CH:21]=1>CN(C)C=O>[S:22]1[CH:23]=[CH:24][C:20]([CH2:19][O:1][C:2]2[CH:11]=[CH:10][C:5]3[S:6][C:7](=[O:9])[O:8][C:4]=3[CH:3]=2)=[CH:21]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 721396-Hydroxy-1,3-benzoxathiol-2-oneHCID 124874623-(Chloromethyl)thiophene

Product 1

HCID 220104656-(3-Thienylmethoxy)-1,3-benzoxathiol-2-oneYield 37.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-hydroxy-1,3-benzoxathiol-2-one (15 g) and potassium carbonate (13.8 g) in dimethylformamide (200 mL) is stirred for 20 minutes, and is then treated, dropwise, with 3-chloromethylthiophene (11.8 g). The mixture is stirred at 60° C. for 16 hours. The reaction mixture is then concentrated in vacuo, and partitioned between water (200 mL) and ethyl acetate (200 mL). The aqueous layer is extracted with ethyl acetate (100 mL) and with diethyl ether (100 mL), and the combined aqueous layers are washed with brine, dried over magnesium sulphate, and evaporated to give a yellow solid, which is recrystallised from ethanol (200 mL) to give 6-(3-thienylmethoxy)-1,3-benzoxathiol-2-one (8.9 g), in the form of pale yellow crystals.

Workup

  1. additionis then treated
  2. stirringThe mixture is stirred at 60° C. for 16 hours
  3. concentrationThe reaction mixture is then concentrated in vacuo
  4. custompartitioned between water (200 mL) and ethyl acetate (200 mL)
  5. extractionThe aqueous layer is extracted with ethyl acetate (100 mL) and with diethyl ether (100 mL)
  6. washthe combined aqueous layers are washed with brine
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customto give a yellow solid, which
  10. customis recrystallised from ethanol (200 mL)

Sources & evidence

ORD record
ord-d339c431f09948629813eca16e91aff5
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211234B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes