Hexane → 5-Bromo-4-tert-butyl-1,3-thiazol-2-amine

HRID 644439Notes

Reaction equation

HRID 644439 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:6]=1.[Br:11]N1C(=O)CCC1=O.CCCCCC>C(Cl)(Cl)(Cl)Cl>[NH2:1][C:2]1[S:3][C:4]([Br:11])=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:6]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 67184N-bromobutanimideHCID 27342024-tert-Butyl-1,3-thiazol-2-amine

Product 1

HCID 7291355-Bromo-4-tert-butyl-1,3-thiazol-2-amineYield 93.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Amino-4-[(1,1-dimethyl)ethyl]thiazole (compound of Example 181(1); 0.87 g, 5.6 mmol) was dissolved in carbon tetrachloride (9 mL). N-Bromosuccinimide (1.00 g, 5.6 mmol) was added, and the mixture was stirred at room temperature for 1 hour. Hexane was added to the reaction mixture. The insoluble matter was filtered off, and the residue obtained by evaporation of the filtrate under reduced pressure was purified by chromatography on silica gel (hexane:ethyl acetate=2:1) to give the title compound (1.23 g, 93.7%) as an yellowish gray powder.

Workup

  1. filtrationThe insoluble matter was filtered off
  2. customthe residue obtained by evaporation of the filtrate under reduced pressure
  3. customwas purified by chromatography on silica gel (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-7a79036d05b44beabd86e65881402ec7
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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