1-(Chloromethoxy)-2-methoxyethane → HCID 53946003, compound

HRID 2187063Notes

Reaction equation

HRID 2187063 reaction equation
[O:1]=[C:2]1[N:11]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10](=[O:21])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:22])[CH:8]=2)[NH:3]1.C(N(CC)C(C)C)(C)C.[CH3:32][O:33][CH2:34][CH2:35][O:36][CH2:37]Cl>ClCCl>[O:1]=[C:2]1[N:11]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10](=[O:21])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:22][CH2:32][O:33][CH2:34][CH2:35][O:36][CH3:37])[CH:8]=2)[NH:3]1

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 54069412HCID 54069412, compound

Product 1

HCID 53946003HCID 53946003, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of ethyl 2,4-dioxo-6-hydroxy-1,2,3,4-tetrahydroquinazoline-3-valerate (3.50 g, 11.8 mmol) obtained in Reference Example 149 in dichloromethane (35.0 ml), N,N-diisopropylethylamine (2.05 ml, 17.7 mmol) and 2-methoxyethoxymethyl chloride (2.02 ml, 17.7 mmol) were added dropwise with cooling on ice, and the reaction mixture was stirred at room temperature for 18 hours. The solvent was distilled off under reduced pressure, and the residue was combined with water and extracted with ethyl acetate. After the extract was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure to give the title compound (3.68 g, 79%). Recrystallization from ethyl acetate-ethyl ether yielded a colorless crystal having a melting point of 105 to 107° C.

Workup

  1. temperaturewith cooling on ice
  2. distillationThe solvent was distilled off under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washAfter the extract was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c40283d318de4eaf8a5fa7a152bf48fe
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

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