Ammonium Chloride → HCID 85815752, compound

HRID 1759922Notes

Reaction equation

HRID 1759922 reaction equation
C(N(C(C)C)CC)(C)C.[CH2:10]([O:14][C:15]1[CH:20]=[C:19](Cl)[N:18]=[CH:17][N:16]=1)[C:11]#[C:12][CH3:13].[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[SH:29].[Cl-].[NH4+]>C(Cl)(Cl)Cl>[CH2:10]([O:14][C:15]1[CH:20]=[C:19]([S:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[Cl:22])[N:18]=[CH:17][N:16]=1)[C:11]#[C:12][CH3:13]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 80599o-ChlorothiophenolHCID 81531DiisopropylethylamineHCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

Product 1

HCID 85815752HCID 85815752, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 5 ml of chloroform were added 0.95 ml of diisopropylethylamine, 0.5 g of 4-(2-butynyloxy)-6-chloropyrimidine, and 0.42 g of 2-chlorothiophenol, followed by stirring at room temperature for 7 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 0.51 g of 4-(2-butynyloxy)-6-(2-chlorothiophenoxy)pyrimidine (the present compound (142)).

Workup

  1. extractionextracted three times with chloroform
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9d0a1479056c4e2993622c3c4f458b17
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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