Thionyl Chloride → HCID 19363243, compound

HRID 850482Notes

Reaction equation

HRID 850482 reaction equation
O[CH2:2][C:3]([NH:6][C:7](=[O:22])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:9]=1)([CH3:5])[CH3:4].S(Cl)(Cl)=O>C(OCC)C>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[O:22][CH2:2][C:3]([CH3:4])([CH3:5])[N:6]=2)=[CH:9][C:10]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19363312HCID 19363312, compound

Product 1

HCID 19363243HCID 19363243, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-(2-Hydroxy-1,1-dimethylethyl)-4-methoxy-3-pentyloxybenzamide (5.498 g, 0.0178 mol, 1 eq) was dissolved in thionyl chloride (4.29 ml, 0.0214 mol, 3.3 eq), and the solution was stirred at room temperature for 1 hour. The reaction mixture was poured into diethyl ether (40 ml). The obtained hydrochloride compound was collected by filtration, and excess thionyl chloride was removed. A 1N aqueous sodium hydroxide solution (about 20 ml) was added to this hydrochloride compound under ice-cooling, whereby the mixture was alkalized (pH=10). The solution was extracted twice with diethyl ether (30 ml). The organic layers were combined, washed with saturated brine (60 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give 2-(4-methoxy-3-pentyloxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole (4.46 g, 86%) as colorless crystals.

Workup

  1. filtrationThe obtained hydrochloride compound was collected by filtration, and excess thionyl chloride
  2. customwas removed
  3. additionA 1N aqueous sodium hydroxide solution (about 20 ml) was added to this hydrochloride compound under ice-
  4. temperaturecooling
  5. extractionThe solution was extracted twice with diethyl ether (30 ml)
  6. washwashed with saturated brine (60 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe drying agent was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1e642c1ccfec43468047e7885068c561
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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