Bromide ion → HCID 71003635, compound

HRID 1468683Notes

Reaction equation

HRID 1468683 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[C:8]([CH3:13])=[CH:7][C:5]=2[N:6]=1.[C:14](ON=O)([CH3:17])(C)[CH3:15].[Br-].COC1C(C)=CC2N=C(N)SC=2C=1>C(#N)C>[CH:17]1([C:2]2[S:3][C:4]3[CH:10]=[C:9]([O:11][CH3:12])[C:8]([CH3:13])=[CH:7][C:5]=3[N:6]=2)[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 259Bromide ionHCID 10906Tert-Butyl nitriteHCID 20289145HCID 20289145, compoundHCID 70981883HCID 70981883, compound

Product 1

HCID 71003635HCID 71003635, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation of (2-bromo-6-methoxy-5-methylbenzo[d]thiazole (6A): To a solution of t-butylnitrite (5.17 ml, 43.5 mmol) in acetonitrile (50 ml) was added coppeer (II) bromide (7.2 g, 32.2 mmol) slowly. The reaction mixture was stirred at room temperature for half hour. Then the reaction mixture was put to a 60° C. oil bath and 6-methoxy-5-methylbenzo[d]thiazol-2-amine (5A) (4.2 g, 21.76 mmol) was added slowly. The reaction mixture was stirred at 60° C. for 1 h. The reaction was cooled to room temperature; washed with water and extracted with EtOAc. The organic phase was combined, dried over MgSO4, filtered, concentrated and purified by silica gel column, eluting by 0-50% EtOAc in hexanes. LCMS-ESI+: calc'd for C9H8BrNOS: 257.9 (M+H+). Found: 258.0 (M+H+).

Workup

  1. customwas put to a 60° C.
  2. stirringThe reaction mixture was stirred at 60° C. for 1 h
  3. temperatureThe reaction was cooled to room temperature
  4. washwashed with water
  5. extractionextracted with EtOAc
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica gel column
  10. washeluting by 0-50% EtOAc in hexanes

Sources & evidence

ORD record
ord-1142e92a8f64444bade3896a5bdaf83a
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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