Sodium hydride → 3-(6-(3-Chloropropoxy)-7-methoxyquinazolin-4-ylthio)aniline

HRID 1918012Notes

Reaction equation

HRID 1918012 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:5]=[C:6]([SH:10])[CH:7]=[CH:8][CH:9]=1.Cl[C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:27][CH3:28])=[C:19]([O:22][CH2:23][CH2:24][CH2:25][Cl:26])[CH:20]=2)[N:15]=[CH:14][N:13]=1>C1COCC1>[Cl:26][CH2:25][CH2:24][CH2:23][O:22][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][C:18]=1[O:27][CH3:28])[N:15]=[CH:14][N:13]=[C:12]2[S:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 315773-AminothiophenolHCID 507422644-Chloro-6-(3-chloropropoxy)-7-methoxyquinazoline

Product 1

HCID 668766163-(6-(3-Chloropropoxy)-7-methoxyquinazolin-4-ylthio)aniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a round bottomed flask, sodium hydride (121 mg, 3.14 mmol), a 60% dispersion in mineral oil, was suspended in 20 mL of dry THF. To this suspension 3-aminothiophenol (394 mg, 3.14 mmol) was added and the reaction stirred for 30 minutes. To this solution 4-chloro-6-(3-chloropropoxy)-7-methoxyquinazoline (900 mg, 3.14 mmol) and the reaction stirred overnight. The reaction was quenched with water, concentrated, and partitioned between water and ethyl acetate. After extracting twice, the extracts were combined, dried over magnesium sulfate, filtered and concentrated to give 3-(6-(3-chloropropoxy)-7-methoxyquinazolin-4-ylthio)aniline as a yellow solid and used without further purification. 1H (DMSO-d6) 8.70 (s, 1H), 7.34 (s, 1H), 7.15 (m, 1H), 6.80 (s, 1H), 6.75 (m, 2H), 4.28 (m, 2H), 3.99 (s, 3H), 3.84 (m, 2H), 2.38 (m, 2H); LCMS (ESI) m/z 376 (M+H).

Workup

  1. customThe reaction was quenched with water
  2. concentrationconcentrated
  3. custompartitioned between water and ethyl acetate
  4. extractionAfter extracting twice
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-57f3b55260a54bcf83bcefbe16f5918f
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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