Water → HCID 68661314, compound

HRID 1022398Notes

Reaction equation

HRID 1022398 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].[H-].[Na+].Cl[C:8]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:24])[CH:14]=2)[N:9]=1.O>CN(C=O)C>[Cl:24][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([S:1][CH2:2][CH2:3][OH:4])[N:17]=[C:16]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15672-MercaptoethanolHCID 24758Sodium hydrideHCID 16282212,6-dichloro-4-phenylquinazoline

Product 1

HCID 68661314HCID 68661314, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 86 mg of 2-mercaptoethanol in DMF (7.5 ml) was added 44 mg of sodium hydride (60%), followed by stirring at room temperature for 30 minutes. To the reaction mixture was added 275 mg of 2,6-dichloro-4-phenylquinazoline (compound No. Ia1-3), followed by stirring at room temperature for 2 hours. The reaction solution was poured into 100 ml of water and extracted with ethyl acetate. The resultant extract was concentrated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5) to obtain 266 mg of the titled compound. Mp.124.4° C. 1H NMR (CDCl3): 3.50 (2H, t, J=5.5 Hz), 3.64 (1H, br. t), 4.07 (2H, q-like, J=5.5 Hz), 7.57-7.61 (3H, m), 7.71-7.74 (2H, m), 7.77 (1H, dd, J=8.9, 2.3 Hz), 7.85 (1H, d, J=8.9 Hz), 7.97 (1H, d, J=2.3 Hz).

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. extractionThe resultant extract
  4. concentrationwas concentrated
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-fc8db45f6e8040259ba780bed449892f
Source dataset
uspto-grants-2014_05
Patent number
US08722580B2

Reaction notes

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