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

HRID 487694Notes

Reaction equation

HRID 487694 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][S:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27]O)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:31])=O.C(=O)([O-])O.[Na+]>CN(C)C=O.C(Cl)(Cl)Cl>[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][S:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27][Cl:31])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 190927354-Tert-butyl-2-[5-(2-hydroxymethylphenylthiomethyl)benzofuran-2-yl]thiazole

Product 1

HCID 190927004-Tert-butyl-2-[5-(2-chloromethylphenylthiomethyl)benzofuran-2-yl]thiazoleYield 136.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 4-tert-butyl-2-[5-(2-hydroxymethylphenylthiomethyl)benzofuran-2-yl]thiazole (0.42 g), thionyl chloride (0.1 g) and N,N-dimethylformamide (3 drops) in chloroform (5 ml) was stirred for 3 hours at ambient temperature. The resulting mixture was poured into aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give 4-tert-butyl-2-[5-(2-chloromethylphenylthiomethyl)benzofuran-2-yl]thiazole (0.49 g).

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd6ecbab1e954832bd33f6cba098e4a1
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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