Dichloromethane → Ethanone, 2-bromo-1-tetrazolo[1,5-a]pyridin-6-yl-

HRID 1004630Notes

Reaction equation

HRID 1004630 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([N:10]=[N:11][N:12]=2)[CH:9]=1)(=[O:3])[CH3:2].Br.C(O)(=O)C.[Br:18]N1C(=O)CCC1=O.ClCCl>C(O)(=O)C.C(OCC)(=O)C>[Br:18][CH2:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([N:10]=[N:11][N:12]=2)[CH:9]=1)=[O:3]

Participants

7

Reactant 4

HCID 6344Dichloromethane2×HCID 67184N-bromobutanimideHCID 130903111-(Tetrazolo[1,5-a]pyridin-6-yl)ethan-1-oneHCID 21893785Acetic Acid Mixture with Hydrobromic Acid2×

Product 1

HCID 13090312Ethanone, 2-bromo-1-tetrazolo[1,5-a]pyridin-6-yl-

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Acetyl tetrazolo[1,5-a] pyridine (10 g, 62 mmol) in acetic acid (160 mL) was treated with 30% HBr/acetic acid (14.7 mL, 247 mmol) at 0° C. N-bromosuccinimide (11 g, 62 mmol) was slowly added and the reaction stirred for 30 minutes. Another 4 equivalents of 30% HBr/acetic acid (14.7 mL, 247 mmol) was slowly added and the reaction was allowed to warm to room temperature. After 3 hours, the reaction was diluted with ethyl acetate (500 mL) and washed with water (3×300 mL). The organic layer was dried (MgSO4), filtered, and concentrated to afford an oil. Hexanes (75 mL) and dichloromethane (10 mL) were added to the oil and reconcentrated to afford a yellow solid (12.8 9, 86%). Rf =0.2 (CH2Cl2); mp 108-110° C.; 1H NMR (300 MHz, CDCl3) δ 10.2 (s, 1 H), 8.29 (dd, J=9, 10 Hz, 1 H), 8.18 (dd, J=8, 10 Hz, 1 H), 5.06 (s, 2 H); MS (EI) m/z 241 (M+).

Workup

  1. waitAfter 3 hours
  2. washwashed with water (3×300 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford an oil
  7. customto afford a yellow solid (12.8 9, 86%)

Sources & evidence

ORD record
ord-066d22db09944bda92048108a341972d
Source dataset
uspto-grants-2000_04
Patent number
US06051586

Reaction notes

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