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

HRID 431797Notes

Reaction equation

HRID 431797 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[S:4][CH:5]=[C:6]([Sn](C)(C)C)[N:7]=1.[Br:13]C1SC=C(Br)N=1.O>CN(C=O)C>[CH3:1][N:2]([CH3:12])[C:3]1[S:4][CH:5]=[C:6]([Br:13])[N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 27632972,4-Dibromo-1,3-thiazoleHCID 18761613HCID 18761613, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
155 °C

Procedure

Synthesis of 2-Dimethylamino-4-trimethylstannylthiazole 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. extractionextracted with ether (2×)
  2. customDrying
  3. custom(MgSO4) and evaporation of the solvents

Sources & evidence

ORD record
ord-79b53aabbe2246828ed9752c6ad4b071
Source dataset
uspto-grants-2003_12
Patent number
US06660758B1

Reaction notes

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