4-Aminothiophenol → HCID 58542087, compound

HRID 81706Notes

Reaction equation

HRID 81706 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.[Cl:11][C:12]1[N:17]=[C:16](Cl)[CH:15]=[CH:14][N:13]=1>O1CCCC1.C(OCC)(=O)C>[Cl:11][C:12]1[N:17]=[C:16]([S:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:3])=[CH:5][CH:6]=2)[CH:15]=[CH:14][N:13]=1

Participants

6

Reactant 3

HCID 145104-AminothiophenolHCID 24758Sodium hydrideHCID 775312,4-Dichloropyrimidine

Product 1

HCID 58542087HCID 58542087, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (60% dispensed in mineral oil, 0.97 g, 24 mmol) in anhydrous tetrahydrofuran (80 mL), was added 4-aminobenzenethiol (2.77 g, 22 mmol) dissolved in tetrahydrofuran (20 mL) over 5 minutes. The mixture was stirred at room temperature for 30 minutes, to this was added a solution of 2,4-dichloropyrimidine (3.00 g, 20 mmol) dissolved in tetrahydrofuran (20 mL) over 5 minutes. The resulting mixture was stirred at room temperature for 64 hours, diluted with ethyl acetate (100 mL), washed with water and brine. After being dried (Na2SO4), the organic solution was concentrated in vacuo. The residue was flash chromatographed on silica gel using 5% of acetone in dichloromethane as eluant to give the product (3.60 g, 75%).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 64 hours
  2. washwashed with water and brine
  3. dry with materialAfter being dried (Na2SO4)
  4. concentrationthe organic solution was concentrated in vacuo
  5. customchromatographed on silica gel using 5% of acetone in dichloromethane as eluant

Sources & evidence

ORD record
ord-6a06d2c7abc24ec28bdbe9f7d19025ac
Source dataset
uspto-grants-2014_09
Patent number
US08846704B2

Reaction notes

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