Thionyl Chloride → HCID 19603774, compound

HRID 1604642Notes

Reaction equation

HRID 1604642 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]([CH:19](O)[CH3:20])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:24])=O.C(=O)([O-])O.[Na+]>ClCCCl>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH:19]([Cl:24])[CH3:20])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 19603716HCID 19603716, compound

Product 1

HCID 19603774HCID 19603774, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-tert-butyl-2-[5-(1-hydroxyethyl)-benzofuran-2-yl]thiazole (1.5 g) and thionyl chloride (0.44 ml) in 1,2 dichloroethane (35 ml) was stirred under reflux for 2 hours. After cooling, the resulting mixture was adjusted to pH 7 with aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give 4-tert-butyl-2-[5-(1-chloroethyl)-benzofuran-2-yl]thiazole (1.31 g).

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureAfter cooling
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9891fd7f53e441efb41423b75583ac45
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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