4-Toluenesulfonyl chloride → HCID 18368356, compound

HRID 379704Notes

Reaction equation

HRID 379704 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:19]=[CH:18][C:8]([NH:9][C:10]([CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:11])=[CH:7][CH:6]=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>N1C=CC=CC=1>[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([O:1][CH2:2][CH2:3][O:4][C:5]2[CH:6]=[CH:7][C:8]([NH:9][C:10]([CH:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)=[O:11])=[CH:18][CH:19]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 18368357HCID 18368357, compound

Product 1

HCID 18368356HCID 18368356, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4′-(2-Hydroxyethoxy)-3,4,5,6-tetrahydro-2H-pyran-4-carboxanilide (5.7 g) solution in pyridine (50 ml) was added with p-toluenesulfonylchloride (4.92 g). The mixture was stirred for 6 hours at room temperature and allowed to stand for one night. The reaction mixture was concentrated under vacuum and dissolved into chloroform (50 ml). This solution was washed water (50 ml) two times. After concentrated under vacuum, the organic layer was added with methanol (50 ml) and mixed. Crystals formed were collected by filtration, washed with water and then dried under vacuum at 60° C. to obtain 4′-[2-(p-toluenesulfonyloxy)ethoxy]-3,4,5,6-tetrahydro-2H-pyran-4-carboxanilide (5.17 g) as yellowish crystal.

Workup

  1. waitto stand for one night
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. dissolutiondissolved into chloroform (50 ml)
  4. washThis solution was washed water (50 ml) two times
  5. concentrationAfter concentrated under vacuum
  6. additionthe organic layer was added with methanol (50 ml)
  7. additionmixed
  8. customCrystals formed
  9. filtrationwere collected by filtration
  10. washwashed with water
  11. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-ccd7bfc1a4a54ff5843302c8a96fc662
Source dataset
uspto-grants-2001_10
Patent number
US06300368B1

Reaction notes

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