Sodium ethanethiolate → 7-(3-(Ethylthio)propoxy)6-methoxyquinazoline

HRID 1838555Notes

Reaction equation

HRID 1838555 reaction equation
[CH2:1]([S-:3])[CH3:2].[Na+].ClC1C=CC(N[C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH2:24][CH2:25][CH2:26]Cl)=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[CH:13][N:12]=2)=C(F)C=1>CN(C=O)C.O>[CH2:1]([S:3][CH2:26][CH2:25][CH2:24][O:23][C:17]1[CH:16]=[C:15]2[C:20]([CH:11]=[N:12][CH:13]=[N:14]2)=[CH:19][C:18]=1[O:21][CH3:22])[CH3:2]

Participants

5

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 109821564-(4-Chloro-2-fluoroanilino)-7-(3-chloropropoxy)-6-methoxyquinazoline

Product 1

HCID 865864637-(3-(Ethylthio)propoxy)6-methoxyquinazolineYield 54.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of sodium ethanethiolate (120 mg, 1.5 mmol) and 4-(4chloro-2-fluoroanilino)7-(3-chloropropoxy)-6-methoxyquinazoline (227 mg, 0.57 mmol) in DMF (10 ml) was stirred and heated at 70° C. for 3 hours. The reaction mixture was allowed to cool, was diluted with water and extracted with ethyl acetate (3×75 ml). The extracts were combined, washed with water (×2), and then brine, and dried (MgSO4). The solvent was removed by evaporation and the residue was recrystallised from ethyl acetate/hexane to give 4chloro-2-fluoroanilino)-7-(3-(ethylthio)propoxy)6-methoxyquinazoline (86 mg, 40%).

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate (3×75 ml)
  3. washwashed with water (×2)
  4. dry with materialbrine, and dried (MgSO4)
  5. customThe solvent was removed by evaporation
  6. customthe residue was recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4d57280bf429409db5d4a382ef42cc98
Source dataset
uspto-grants-2004_01
Patent number
US06673803B2

Reaction notes

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