Bromine → HCID 86633157, compound

HRID 1926430Notes

Reaction equation

HRID 1926430 reaction equation
BrBr.[CH3:3][C:4]1[CH:5]=[CH:6][C:7]([C:14]([F:17])([F:16])[F:15])=[C:8]([NH:10][C:11]([NH2:13])=[S:12])[CH:9]=1>C(Cl)Cl>[NH2:13][C:11]1[S:12][C:9]2[C:4]([CH3:3])=[CH:5][CH:6]=[C:7]([C:14]([F:17])([F:15])[F:16])[C:8]=2[N:10]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 86633158HCID 86633158, compound

Product 1

HCID 86633157HCID 86633157, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromine in dichloromethane (3.4 mL, 1.0M in DCM, 1.0 eq) was added dropwise to a solution of (5-methyl-2-trifluoromethylphenyl)-thiourea (800 mg, 3.4 mmol, 1.0 eq) in dry DCM (100 mL) below 30° C. The reaction mixture was heated at reflux for 3 h and cooled to room temp. A precipitate was collected by filtration, then suspended in water (20 mL), and the pH was adjusted to 11 with NH4OH. The mixture was then extracted with ethyl acetate (3×20 mL), and the combined organic layers were washed with water (30 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The brown residue was purified by column chromatography on silica gel (eluted by 1% methanol in DCM) to afford 2-amino-7-methyl-4-trifluoromethyl-1,3-benzothiozole as white solid. 1H-NMR (CDCl3, 300 MHz): δ=7.53 (d, J=8.4, 1H), 7.15 (d, J=8.4, 1H), 5.76 (brs, 2H), 2.59 (s, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. filtrationA precipitate was collected by filtration
  4. extractionThe mixture was then extracted with ethyl acetate (3×20 mL)
  5. washthe combined organic layers were washed with water (30 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe brown residue was purified by column chromatography on silica gel (eluted by 1% methanol in DCM)
  10. customto afford 2-amino-7-methyl-4-trifluoromethyl-1,3-benzothiozole as white solid

Sources & evidence

ORD record
ord-9aebf9dd22ec4aee9d9213b06630babb
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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