Water → 4-Chloro-6,7-bis(2-methoxyethoxy)quinazoline

HRID 1797887Notes

Reaction equation

HRID 1797887 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[N:12]=[CH:11][NH:10][C:9]2=O.CN(C)C=O.C(Cl)(=O)C([Cl:30])=O.O>ClCCl>[Cl:30][C:9]1[C:8]2[C:13](=[CH:14][C:15]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:7]=2)[N:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1354093056,7-Bis(2-methoxyethoxy)quinazolin-4(1H)-one

Product 1

HCID 112899424-Chloro-6,7-bis(2-methoxyethoxy)quinazolineYield 126.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 22 (2.60 g, 8.83 mmol) in dichloromethane (25 mL), was added a drop of N,N-Dimethyl formamide and to that oxalyl chloride (1.52 mL, 17.669 mmol) was added dropwise. This mixture was stirred at room temperature for 12 h. Reaction was monitored by TLC and the reduction continued until TLC indicated no starting material. The reaction mixture was poured in to water. Extracted with ethyl acetate and the combined organic layer were washed with Sat.NaHCO3 and brine and dried over Na2SO4 and evaporated to give the crude compound 23 (3.5 g, crude), which was used in the next reaction without further purification.

Workup

  1. customReaction
  2. extractionExtracted with ethyl acetate
  3. washthe combined organic layer were washed with Sat
  4. dry with materialNaHCO3 and brine and dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-f48143b0895f4edd96fd9c0fed0cdae7
Source dataset
uspto-grants-2013_01
Patent number
US08343950B2

Reaction notes

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