4-Toluenesulfonyl chloride → HCID 131735474, compound

HRID 633723Notes

Reaction equation

HRID 633723 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][C:11]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)([CH3:14])[CH2:12][OH:13].C[C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>ClCCl>[C:25]1([S:28]([O:13][CH2:12][C:11]([CH3:10])([C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)[CH3:14])(=[O:30])=[O:29])[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 134781392-Methyl-2-(pyridin-4-yl)propan-1-ol

Product 1

HCID 131735474HCID 131735474, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

710 μl (4.07 mmol) of N,N-diisopropylethylamine and 33.13 mg (0.27 mmol) of 4-dimethyl amino pyridine are added to a solution of 410 mg (2.71 mmol) of 2-methyl-2-pyrid-4-ylpropan-1-ol in 10 mL of dichloromethane. The mixture is cooled to 0° C. and a solution of 775.42 mg (4.07 mmol) of 4-methylbenzene-1-sulfonyl chloride in 2 mL of dichloromethane is then added. After allowing the reaction medium to warm to room temperature and stirring overnight, it is washed with water and with saturated NaCl solution. The organic phase is dried over magnesium sulfate and evaporated to dryness to give 660 mg of 2-methyl-2-pyrid-4-ylpropyl benzenesulfonate, corresponding to the following characteristics:

Workup

  1. temperatureto warm to room temperature
  2. washit is washed with water and with saturated NaCl solution
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-15b0a50593ef459fa1163f78cefb7f42
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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