Bromine → HCID 57634025, compound

HRID 2109736Notes

Reaction equation

HRID 2109736 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:13])[CH3:12])[S:8][CH:9]=1)[CH3:3].[Br:14]Br>CC(O)=O>[Br:14][C:9]1[S:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[N:6][C:5]=1[CH2:4][N:2]([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 57634222N-[4-[(Dimethylamino)methyl]-2-thiazolyl]acetamide

Product 1

HCID 57634025HCID 57634025, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of N-(4-((dimethylamino)methyl)thiazol-2-yl)acetamide (1.1 g, 5.5 mmol) in 10 mL AcOH was added Br2 (0.28 mL, 5.5 mmol) dropwise. The resulting mixture discolored instantly, and a precipitate appeared. The precipitate was filtered and washed with AcOH. The collected precipitate was neutralized with saturated sodium bicarbonate and extracted twice with 100 mL EtOAc. The organic layer was combined, washed once with brine, and dried over sodium sulfate. After removing the solvent, the product was obtained as a white solid (1.0 g, yield=65%). LCMS (API-ES) m/z (%) 278.0 (100%, M++H). 1H NMR (400 MHz, CDCl3) δ ppm 2.24 (s, 3H) 2.28 (s, 6H) 3.44 (s, 2H).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with AcOH
  3. extractionextracted twice with 100 mL EtOAc
  4. washwashed once with brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removing the solvent

Sources & evidence

ORD record
ord-05ba5e9204e246c8b635ec0b4fe99485
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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