Hydrochloric Acid → HCID 22565365, compound

HRID 2202600Notes

Reaction equation

HRID 2202600 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.Cl>C(OCC)C>[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]([C:2]2[S:3][CH:4]=[CH:5][N:6]=2)[OH:13])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 77264-ChlorobenzaldehydeHCID 764302-Bromothiazole

Product 1

HCID 22565365HCID 22565365, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-30 °C

Procedure

A solution of 5.003 g of 2-bromothiazole in 20 mL of diethyl ether was added dropwise to 23 mL of a 1.6-M n-butyllithium/n-hexane solution in 20 mL of diethyl ether under cooling at −30° C. After the mixture was stirred for 1.1 hours, a solution of 5.538 g of 4-chlorobenzaldehyde in 20 mL of diethyl ether was added dropwise thereto. It took 1.2 hours to bring back to a room temperature, and then the reaction solution was poured into a mixture of 72 mL of 1-N hydrochloric acid and ice. The insoluble matter was removed by filtration, and then the organic layer was collected by separation. The organic layer was washed with a saturated sodium bicarbonate water and with saturated saline solution in this order. The organic layer was dried over magnesium sulfate, and then the solvent was distilled off. The raw product was purified by silica gel column chromatography (hexane/ethyl acetate (volume ratio)=2:1 to 3:2) to give the title compound (4.425 g (64%)).

Workup

  1. waitIt took 1.2 hours
  2. customto bring back to a room temperature
  3. customThe insoluble matter was removed by filtration
  4. customthe organic layer was collected by separation
  5. washThe organic layer was washed with a saturated sodium bicarbonate water and with saturated saline solution in this order
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThe raw product was purified by silica gel column chromatography (hexane/ethyl acetate (volume ratio)=2:1 to 3:2)

Sources & evidence

ORD record
ord-aa74db04914f4756bb758ead10e0e742
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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