Water → 2-[4-(2-Bromoethoxy)-3-propylphenyl]-4-ethyl-1,3-thiazole

HRID 603387Notes

Reaction equation

HRID 603387 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([CH2:15][CH2:16][CH3:17])[CH:9]=2)[S:6][CH:7]=1)[CH3:2].O.[Br:19][CH2:20][CH2:21]Br>CN(C=O)C>[Br:19][CH2:20][CH2:21][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[S:6][CH:7]=[C:3]([CH2:1][CH3:2])[N:4]=2)=[CH:9][C:10]=1[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 78391,2-DibromoethaneHCID 1360297904-(4-Ethyl-1,3-thiazol-2-yl)-2-propylphenol

Product 1

HCID 593005482-[4-(2-Bromoethoxy)-3-propylphenyl]-4-ethyl-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-ethyl-1,3-thiazol-2-yl)-2-propylphenol (0.24 g, 0.97 mmol) (Example 33) in DMF (2 mL, containing 1% v/v of water) was added 1,2-dibromoethane (1.09 g, 5.82 mmol), and the mixture was stirred at rt for 12 h. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The crude residue was suspended in EtOAc, filtered through a small plug of silica, and the filtrate was concentrated. The crude material was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 7.79-7.68 (m, 2H), 6.88-6.78 (m, 2H), 4.34 (t, 2H), 3.69 (t, 2H), 2.95-2.82 (m, 2H), 2.72-2.60 (m, 2H), 1.80-1.64 (m, 2H), 1.36 (t, 3H), 1.02 (t, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. filtrationfiltered through a small plug of silica
  4. concentrationthe filtrate was concentrated
  5. customThe crude material was used in the next step without further purification

Sources & evidence

ORD record
ord-be5209adbf124206b4194a7a8d77519e
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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