Thionyl Chloride → HCID 19603727, compound

HRID 487689Notes

Reaction equation

HRID 487689 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]O)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:23])=O.C(=O)([O-])O.[Na+]>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][Cl:23])=[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 190927534-Tert-butyl-2-(5-hydroxymethylbenzofuran-2-yl)thiazole

Product 1

HCID 19603727HCID 19603727, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-tert-butyl-2-(5-hydroxymethylbenzofuran-2-yl)thiazole (2.82 g) and thionyl chloride (1.4 ml) in dichloromethane (30 ml) was stirred under reflux for 1 hour. After being cooled, the resulting mixture was adjusted to pH 7 with aqueous sodium hydrogen carbonate. The organic layer was separated, washed with brine, dried over magnesium sulfate, concentrated under reduced pressure to give crystals of 4-tert-butyl-2-(5-chloromethylbenzofuran-2-yl)thiazole (2.93 g).

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureAfter being cooled
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c34bc86841ba451da9db832d2db112c6
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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