4-Methyloxybenzyl chloride → HCID 11724851, compound

HRID 2210229Notes

Reaction equation

HRID 2210229 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]=[C:5]2[CH:13]1[CH2:15][CH2:14]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Cl)=[CH:30][CH:29]=1>CN(C=O)C.CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:32][C:31]1[CH:34]=[CH:35][C:28]([O:27][CH3:26])=[CH:29][CH:30]=1)[C:7](=[O:12])[N:6]=[C:5]2[CH:13]1[CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 699934-Methyloxybenzyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 178517395HCID 178517395, compound

Product 1

HCID 11724851HCID 11724851, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a 0° C. solution of 9.0 g (0.04 1 mol) of 6-chloro-4-cyclopropylquinazolin-2(1H)-one in 150 mL of dry DMF (Aldrich Sure-Seal) under Ar was added 42.5 mL of a 1.0M solution of lithium bis(trimethylsilyl)amide in hexane dropwise. After the addition, 8.14 mL (0.06 mol) of p-methoxybenzyl chloride (Aldrich) was added in one portion, and the flask immersed in an oil bath maintained at 55°-60° C. The reaction was heated for 12.5 h, then allowed to stand at room temperature overnight. The solvents were removed by rotovap at reduced pressure and the residue partitioned between CHCl3 and cold 1M citric acid. The aqueous layer was extracted with CHCl3 and the combined organic layers washed with 10% Na2CO3, dried over MgSO4. After removal of the solvents by rotovap at reduced pressure, the residue was triturated with ether to give 10.5 g (75%) of the title compound as a light yellow solid.

Workup

  1. additionwas added in one portion
  2. customthe flask immersed in an oil bath
  3. temperaturemaintained at 55°-60° C
  4. temperatureThe reaction was heated for 12.5 h
  5. customThe solvents were removed by rotovap at reduced pressure
  6. customthe residue partitioned between CHCl3 and cold 1M citric acid
  7. extractionThe aqueous layer was extracted with CHCl3
  8. washthe combined organic layers washed with 10% Na2CO3
  9. dry with materialdried over MgSO4
  10. customAfter removal of the solvents by rotovap at reduced pressure
  11. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-4dfca94b865f46caa362ba51bf104091
Source dataset
uspto-grants-1995_10
Patent number
US05457201

Reaction notes

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