Acetic Acid → 5-bromo-N-(pyridin-2-yl)thiazol-2-amine

HRID 1355432Notes

Reaction equation

HRID 1355432 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][CH:10]=[CH:11][N:12]=1.C(O)(=O)C.[Br:17]Br.C([O-])(O)=O.[Na+]>O>[Br:17][C:10]1[S:9][C:8]([NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:12][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 516892Sodium BicarbonateHCID 956683N-(pyridin-2-yl)thiazol-2-amine

Product 1

HCID 53294005-bromo-N-(pyridin-2-yl)thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask containing pyridin-2-yl-thiazol-2-yl-amine (5-2, 3.92 g, 0.0221 mol) was added acetic acid. Bromine (1.14 mL, 0.0221 mol) was then added dropwise to the stirred solution at ambient temperature. The reaction was stirred for 15 min, resulting in an orange-white precipitate. At 15 min, 100 mL H2O were added and solid NaHCO3 introduced, causing a large amount of foaming. The product was obtained as a tan colored precipitate, which was washed with 1.5 L H2O and dried under high vacuum overnight. 1H NMR (DMSO-d6): δ11.53 (bs, 1H), 8.31 (d, 1H, J=3.3 Hz), 7.73 (t, 1H, J=7.6 Hz), 7.45 (s, 1H), 7.05 (d, 1H, J=8.4 Hz), 6.96 (t, 1H, J=5.5 Hz). Mp: 210-212° C. (dec). [M+H]+=255.9.

Workup

  1. customresulting in an orange-white precipitate
  2. waitAt 15 min
  3. customThe product was obtained as a tan colored precipitate, which
  4. washwas washed with 1.5 L H2O
  5. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-7ecf22ce74554acba20c68a61e7807b9
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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