Thionyl Chloride → 4-Tert-butyl-2-[5-(3-chloropropyl)benzofuran-2-yl]thiazole

HRID 1604637Notes

Reaction equation

HRID 1604637 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21]O)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:25])=O>ClCCl>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][Cl:25])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 196037673-[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yl]propanol

Product 1

HCID 196037484-Tert-butyl-2-[5-(3-chloropropyl)benzofuran-2-yl]thiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]propanol (0.40 g) and thionyl chloride (0.4 ml) in dichloromethane (5 ml) was stirred under reflux for 5 hours. After being cooled to room temperature, the solution was concentrated under reduced pressure. The resulting residue -was partitioned between aqueous sodium hydrogencarbonate solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a 4-tert-butyl-2-[5-(3-chloropropyl)benzofuran-2-yl]thiazole (0.28 g).

Workup

  1. temperatureunder reflux for 5 hours
  2. concentrationthe solution was concentrated under reduced pressure
  3. customThe resulting residue -was partitioned between aqueous sodium hydrogencarbonate solution and ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a5b53cd814544098d297d65e46d8104
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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