Hydrochloric Acid → HCID 13362008, compound

HRID 1632607Notes

Reaction equation

HRID 1632607 reaction equation
[CH2:1]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[CH:11]([CH2:21][OH:22])[CH2:10][C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K].[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.Cl>>[CH2:1]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[CH:11]([CH2:21][O:22][S:31]([C:28]2[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=2)(=[O:33])=[O:32])[CH2:10][C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 5462222PotassiumHCID 13362007HCID 13362007, compound

Product 1

HCID 13362008HCID 13362008, compound

Procedure

To 21.4 gm. of 1-benzyl-4-hydroxymethyl-5-(3methoxyphenyl)pyrrolidin-2-one in 40 ml. of potassium dried pyridine was slowly added at -4° to -7°, 14.4 gm of p-toluenesulfonyl chloride. The reaction mixture was stirred for 3 hours at 15° and then diluted with 180 ml. of 10% hydrochloric acid. The gum was extracted with chloroform, dried (Na2SO4), filtered and concentrated in vacuo to provide 24.6 gm. of the desired product as an oil.

Workup

  1. additiondiluted with 180 ml
  2. extractionThe gum was extracted with chloroform
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide 24.6 gm

Sources & evidence

ORD record
ord-0e9042cdb6d6433f9f2c019048460b8a
Source dataset
uspto-grants-1984_10
Patent number
US04476311

Reaction notes

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