4-Toluenesulfonyl chloride → HCID 19046793, compound

HRID 1781638Notes

Reaction equation

HRID 1781638 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[N:12]1[CH:17]=[C:16]([CH2:18][CH2:19][CH2:20][OH:21])[CH:15]=[N:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)([O:21][CH2:20][CH2:19][CH2:18][C:16]1[CH:17]=[N:12][CH:13]=[N:14][CH:15]=1)(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 190467243-(Pyrimidin-5-yl)propan-1-ol

Product 1

HCID 19046793HCID 19046793, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

9.87 g (51.7 mmol) of tosyl chloride in 50 ml of dichloromethane are added dropwise at room temperature to a solution of 6.5 g (47 mmol) of 3-(pyrimidin-5-yl)propanol and 9 ml (64.6 mmol) of triethylamine in 100 ml dichloromethane that is being stirred under nitrogen. The mixture is stirred for 16 hours at room temperature, then washed with water and saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated by evaporation under reduced pressure. 14.42 g of 3-(pyrimidin-5-yl)propyl tosylate are obtained, which can be processed further without further purification.

Workup

  1. stirringThe mixture is stirred for 16 hours at room temperature
  2. washwashed with water and saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-090ab9c6b546451287c6d7bb1a779f17
Source dataset
uspto-grants-1997_05
Patent number
US05633379

Reaction notes

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