Sodium Hydroxide → HCID 18407006, compound

HRID 1016392Notes

Reaction equation

HRID 1016392 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:25][CH2:26][CH2:27]OC)=[C:17](OCCOC)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)[CH3:2].[OH-:30].[Na+]>C(O)C1C=CC=CC=1>[CH2:8]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:25][CH2:26][C:27]4[CH:7]=[CH:8][CH:3]=[CH:1][CH:2]=4)=[C:17]([O:30][CH2:15][CH2:16][O:25][CH3:26])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:2][CH:1]=1)[CH3:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 6710785HCID 6710785, compound

Product 1

HCID 18407006HCID 18407006, compound

Reagents, catalysts & solvents 1

HCID 244Benzyl AlcoholSolvent

Conditions

Temperature
151 °C

Procedure

N-(3-ethylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine, prepared as described above (4.0 g, 10 mmol), solid anhydrous sodium hydroxide (104 mg, 2.6 mmol) and benzyl alcohol (20 mL) was heated at 150-152° C. for 23 hours. The reaction mixture was allowed to cool to room temperature and purified by column chromatography on silica gel using a gradient system with ethyl acetate/hexane as eluent to give a white solid which was dried under vacuum at 45-50° C. to give the title product. (2.52 g, 58%), mp 156-157° C.

Workup

  1. temperatureto cool to room temperature
  2. custompurified by column chromatography on silica gel using a gradient system with ethyl acetate/hexane as eluent
  3. customto give a white solid which
  4. customwas dried under vacuum at 45-50° C.

Sources & evidence

ORD record
ord-a4d537702b0f4483b8566fb8e09dfd77
Source dataset
uspto-grants-2002_11
Patent number
US06476040B1

Reaction notes

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