Hydrochloric Acid → HCID 57999644, compound

HRID 600318Notes

Reaction equation

HRID 600318 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][OH:21].Cl>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][OH:21])[C:6]=2[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 28012735-Bromobenzo[d]thiazol-2(3H)-one

Product 1

HCID 57999644HCID 57999644, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromobenzo[d]thiazol-2(3H)-one (1 g) and potassium carbonate (1.5 g) were stirred in DMF (7 mL) at room temperature and 2-bromoethanol (0.4 mL) added. The mixture was stirred for 48 h. The mixture was poured onto water and acidified with dilute hydrochloric acid 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 25% ethyl acetate in isohexane afforded the subtitle compound as a colourless solid (0.540 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 25% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-c193cad11d1a4764a1b00d6080f57ef4
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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