4-Toluenesulfonyl chloride → HCID 86739786, compound

HRID 1153965Notes

Reaction equation

HRID 1153965 reaction equation
OCCC[N:5]1C(=O)N(CCOC2C=CC=CC=2)C(CC)=[N:6]1.[S:22]([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)([O-:25])(=[O:24])=[O:23].C([N:35](CC)[CH2:36][CH3:37])C.S(Cl)(C1C=CC(C)=CC=1)(=O)=[O:41]>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[S:22]([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)([OH:25])(=[O:24])=[O:23].[N:35]1[N:5]=[N:6][C:37](=[O:41])[CH:36]=1

Participants

8

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 85570p-ToluenesulfonateHCID 10379527HCID 10379527, compound

Product 1

HCID 86739786HCID 86739786, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The alcohol is converted to the tosylate by dissolving in methylene chloride containing N,N-dimethyl-4-aminopyridine (0.05 mol eq) and triethylamine (1.05 mol eq) and treating with tosyl chloride (1.1 mole eq) added in one portion at 0° C. with stirring. After standing for about 24 hr. at 0° C., the mixture is treated with water and extracted several times with methylene chloride. The combined methylene chloride extracts are dried over magnesium sulfate, filtered and concentrated under reduced pressure. Flash chromatography of residual material affords 2-[3-(p-toluenesulfonate)propyl]-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one (XV, Y=H, X1 =0, n=2, R2 =C2H5).

Workup

  1. additionadded in one portion at 0° C.
  2. extractionextracted several times with methylene chloride
  3. dry with materialThe combined methylene chloride extracts are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ca12cd3df928430db815c350cc4a9720
Source dataset
uspto-grants-1984_12
Patent number
US04487773

Reaction notes

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