Hydrochloric Acid → 4-Fluoro-2-(isopropylamino)benzo[d]thiazole-6-carbaldehyde

HRID 1671786Notes

Reaction equation

HRID 1671786 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[C:7]([F:13])[C:5]=2[N:6]=1.[CH:14]([NH2:17])([CH3:16])[CH3:15].Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[F:13][C:7]1[C:5]2[N:6]=[C:2]([NH:17][CH:14]([CH3:16])[CH3:15])[S:3][C:4]=2[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6363IsopropylamineHCID 516892Sodium BicarbonateHCID 575272232-Bromo-4-fluorobenzo[d]thiazole-6-carbaldehyde

Product 1

HCID 575272374-Fluoro-2-(isopropylamino)benzo[d]thiazole-6-carbaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-bromo-4-fluorobenzo[d]thiazole-6-carbaldehyde (0.110 g, 0.423 mmol) and isopropylamine (0.15 ml, 1.76 mmol) in 1,4-dioxane (5 mL) was heated at reflux for 36 hr. The solution was allowed to cool to rt and 1N HCl (1 mL) was added. The mixture was heated at 60° C. for 1 hr. After it cooled to rt, the mixture was poured into saturated NaHCO3 solution (20 mL) and extracted with AcOEt (3×25 mL). The combined extract was dried over anhydrous MgSO4 and concentrated to dryness under vacuum to provide the title crude compound, which was used in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 36 hr
  3. temperatureThe mixture was heated at 60° C. for 1 hr
  4. temperatureAfter it cooled to rt
  5. extractionextracted with AcOEt (3×25 mL)
  6. extractionThe combined extract
  7. dry with materialwas dried over anhydrous MgSO4
  8. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-82b4d4f72fd74226b535e9a1041e506f
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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