Potassium Carbonate → HCID 57999633, compound

HRID 216925Notes

Reaction equation

HRID 216925 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][O:21][CH3:22]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:19][CH2:20][O:21][CH3:22])[C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 28012735-Bromobenzo[d]thiazol-2(3H)-one

Product 1

HCID 57999633HCID 57999633, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromobenzo[d]thiazol-2(3H)-one (1 g) and potassium carbonate (1.502 g) were stirred in DMF (7 mL) at room temperature and 1-bromo-2-methoxyethane (0.408 mL) was added. The mixture was stirred for 24 h. The mixture was poured onto water and extracted with ethyl acetate. The extracts were washed with dilute hydrochloric acid, water and brine then dried over sodium sulfate and evaporated. Purification by flash silica chromatography eluting with 10% ethyl acetate in isohexane afforded the sub-titled compound as a colourless solid (0.73 g).

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with dilute hydrochloric acid, water and brine
  4. dry with materialthen dried over sodium sulfate
  5. customevaporated
  6. customPurification by flash silica chromatography
  7. washeluting with 10% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-7ecf7fad0ea443cea96e2b714906f343
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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