Water → 4-Bromo-N,N-dimethyl-1,3-thiazol-2-amine

HRID 347410Notes

Reaction equation

HRID 347410 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([Br:7])[N:6]=1.O.[CH3:9][N:10](C=O)[CH3:11]>>[CH3:9][N:10]([CH3:11])[C:2]1[S:3][CH:4]=[C:5]([Br:7])[N:6]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 27632972,4-Dibromo-1,3-thiazole

Product 1

HCID 187616024-Bromo-N,N-dimethyl-1,3-thiazol-2-amineYield 89%

Procedure

Synthesis of 2-Dimethylamino-4-tremthylstannylthiazole 386 as illustrated in FIG. 53. 2,4-Dibromothiazole (358; 1.0 equiv) was dissolved in DMF (0.1 M) and heated at 150–160° C. for 8 h, upon which completion of the reaction was indicated by TLC. The mixture was poured into water and extracted with ether (2×). Drying (MgSO4) and evaporation of the solvents gave 2-dimethylamino-4-bromothiazole 385, which was isolated after flash column chromatography (silica gel, 5% EtOAc in hexanes) in 89% yield.

Workup

  1. temperatureheated at 150–160° C. for 8 h, upon which completion of the reaction
  2. extractionextracted with ether (2×)
  3. customDrying
  4. custom(MgSO4) and evaporation of the solvents

Sources & evidence

ORD record
ord-475e3856974d4592bdfc220950d943ec
Source dataset
uspto-grants-2007_02
Patent number
US07173137B2

Reaction notes

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