4-Toluenesulfonyl chloride → HCID 86676467, compound

HRID 532126Notes

Reaction equation

HRID 532126 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH2:7][C:6]2=[N:13][OH:14].[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>N1C=CC=CC=1>[S:22]([O:14][N:13]=[C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[O:9][CH2:8][CH2:7]1)([C:19]1[CH:20]=[CH:21][C:16]([CH3:15])=[CH:17][CH:18]=1)(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 85960732HCID 85960732, compound

Product 1

HCID 86676467HCID 86676467, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

5.68 g (29.4 mmol) of 6-methoxychroman-4-one oxime were dissolved under argon atmosphere in 30 ml of dry pyridine. At 0° C. 6.05 g (31.8 mmol) of 4-methylbenzene-1-sulfonyl chloride were added in small portions over 40 min. The mixture was stirred at 0° C. for an additional hour and then warmed to room temperature and stirred over night. The mixture was poured onto 260 ml ice water, stirred, and the suspension was filtered. The solid residue was washed with a small amount of cold water (2×) and cold ethanol (1×), and dried to yield 8.96 g (25.8 mmol, 88%) of desired product.

Workup

  1. customAt 0° C
  2. temperaturewarmed to room temperature
  3. stirringstirred over night
  4. stirringstirred
  5. filtrationthe suspension was filtered
  6. washThe solid residue was washed with a small amount of cold water (2×) and cold ethanol (1×)
  7. customdried

Sources & evidence

ORD record
ord-36e28c5a7bef42e3a2a63fcb3acf46bb
Source dataset
uspto-grants-2014_10
Patent number
US08853196B2

Reaction notes

Loading…