Thionyl Chloride → 4,4-Dimethyl-2-(4'-chloromethylbiphenyl-2-yl)oxazoline

HRID 53429Notes

Reaction equation

HRID 53429 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([CH2:19]O)=[CH:15][CH:14]=2)=[N:3]1.S(Cl)([Cl:24])=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1([CH3:21])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][Cl:24])=[CH:15][CH:14]=2)=[N:3]1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 110658764,4-Dimethyl-2-(4'hydroxymethylbiphenyl-2-yl)oxazoline

Product 1

HCID 109794774,4-Dimethyl-2-(4'-chloromethylbiphenyl-2-yl)oxazolineYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.0 g (3.55 mmol) of 4,4-dimethyl-2-(4'-hydroxymethylbiphenyl-2-yl)oxazoline was dissolved in methylene chloride (15 ml). Under cooling with ice, 0.51 g (4.29 mmol) of thionyl chloride was dropwise added thereto, followed by stirring for one hour. The reaction liquid was poured into an aqueous solution of sodium hydrogencarbonate, followed by the extraction with methylene chloride. After washing with water and drying, vacuum concentration was conducted. 1.05 g of the title compound was obtained as a crystal (yield 99%).

Workup

  1. additionwas dropwise added
  2. customThe reaction liquid
  3. extractionfollowed by the extraction with methylene chloride
  4. washAfter washing with water
  5. customdrying
  6. concentrationvacuum concentration

Sources & evidence

ORD record
ord-dc90f2fc2dfe4961b6442627198b000c
Source dataset
uspto-grants-1997_04
Patent number
US05618969

Reaction notes

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