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Potassium Carbonate → (S)-4-glycidyloxy-N,N-dimethylbenzo(b)thiophene-2-carboxamide

HRID 460557
Notes
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Reaction equation

HRID 460557 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([O:14][CH2:15]O)[C:7]=2[CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].S(C1C=CC([N+]([O-])=O)=CC=1)(OC[C@H:29]1[O:31][CH2:30]1)(=O)=O>CN(C=O)C>[CH2:15]([O:14][C:13]1[C:7]2[CH:6]=[C:5]([C:3]([N:2]([CH3:17])[CH3:1])=[O:4])[S:9][C:8]=2[CH:10]=[CH:11][CH:12]=1)[C@H:30]1[O:31][CH2:29]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10868995(S)-(+)-Glycidyl-4-nitrobenzoateHCID 22729338N,N-dimethyl-4-(hydroxymethyloxy)benzo(b)thiophene-2-carboxamide

Product 1

HCID 60078007(S)-4-glycidyloxy-N,N-dimethylbenzo(b)thiophene-2-carboxamideYield 87.6%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
60 °C

Procedure

To a solution of N,N-dimethyl-4-(hydroxymethyloxy)benzo(b)thiophene-2-carboxamide (9.0 g) in DMF (100 ml) was added potassium carbonate (8.0 g), and (S)-glycidyl nosylate (8.0 g) was further added. The mixture was stirred at 60° C. for 2 hr. The reaction mixture was concentrated under reduced pressure and water was added. The mixture was extracted with ethyl acetate and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained crystals were recrystallized from ethyl acetate to give the title compound (7.5 g).

Workup

  1. additionwas further added
  2. concentrationThe reaction mixture was concentrated under reduced pressure and water
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2b67132adc8042ac843d0737ab80b740
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07196199B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes