4-Toluenesulfonyl chloride → HCID 20148844, compound

HRID 1632623Notes

Reaction equation

HRID 1632623 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][C:6](=[O:8])[N:5]([CH3:9])[CH:4]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[K+].[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>>[CH3:9][N:5]1[C:6](=[O:8])[CH2:7][CH:3]([CH2:2][O:1][S:24]([C:21]2[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=2)(=[O:26])=[O:25])[CH:4]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 13362032HCID 13362032, compound

Product 1

HCID 20148844HCID 20148844, compound

Conditions

Temperature
15 °C

Procedure

To 27.8 g. of 3-hydroxymethyl-1-methyl-2-phenylpyrrolidin-5-one in 40 ml. of potassium hydroxide dried pyridine was added in portions at 0°-5° 29.4 g. of p-toluenesulfonyl chloride. The orange solution was then stirred at 15° C. for 4 hours and then decanted into 180 ml. of ice cold 10% hydrochloric acid. The resulting solid was collected by filtration and washed with water and air dried. Washing with ether provided 37 g. of crude product.

Workup

  1. customdecanted into 180 ml
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water and air
  4. customdried
  5. washWashing with ether
  6. customprovided 37 g

Sources & evidence

ORD record
ord-5ab779cda10649c695a31c6b9261571a
Source dataset
uspto-grants-1984_10
Patent number
US04476311

Reaction notes

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