Bromine → HCID 68285300, compound

HRID 1497665Notes

Reaction equation

HRID 1497665 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C([O-])(=O)C.[Na+].[Br:26]Br>C(O)(=O)C.[OH-].[Na+]>[Br:26][C:14]1[S:13][C:12]([CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[N:11][C:10]=1[C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

6

Reactant 3

HCID 24408Bromine2×HCID 517045Sodium AcetateHCID 68285207HCID 68285207, compound

Product 1

HCID 68285300HCID 68285300, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 4-(3-nitrophenyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazole (113 mg, 0.390 mmol) in acetic acid (10.5 mL), sodium acetate (71 mg, 0.866 mmol, 2.2 eq.) was added, and the mixture stirred for 30 min. To the solution so obtained, bromine was added dropwise and the reaction followed by HPLC up to completion (total Br2: 44 μL, 137 mg, 0.86 mmol, 2.2 eq). The solution was poured in 100 mL of 1M sodium hydroxide and extracted three times with ethyl acetate. The organic layer was washed with brine, dried up with sodium sulfate and evaporated to dryness to yield 5-bromo-4-(3-nitrophenyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazole (141 mg, 100%)

Workup

  1. customTo the solution so obtained
  2. extractionextracted three times with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried up with sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-05df41c5640b4dd295168b77dc19ff4c
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

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