Thiophenol → HCID 85815847, compound

HRID 1759885Notes

Reaction equation

HRID 1759885 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]#[C:11][CH3:12])[N:5]=[CH:4][N:3]=1.[C:13]1([SH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:9]([O:8][C:6]1[CH:7]=[C:2]([S:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=[CH:4][N:5]=1)[C:10]#[C:11][CH3:12]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 25517Ammonium ChlorideHCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Product 1

HCID 85815847HCID 85815847, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

To 5 ml of chloroform were added 0.57 ml of triethylamine and 0.5 g of 4-chloro-6-(2-butynyloxy)pyrimidine, to which 0.6 ml of a chloroform solution containing 0.33 g of thiophenol was slowly added dropwise, followed by stirring at room temperature for 8 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.22 g of 4-(2-butynyloxy)-6-(thiophenoxy)pyrimidine (the present compound (97)).

Workup

  1. additionwas slowly added dropwise
  2. extractionextracted three times with chloroform
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-50b8c4b59bd644ba92cdd717443e874c
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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