4-Toluenesulfonyl chloride → HCID 22118462, compound

HRID 1275457Notes

Reaction equation

HRID 1275457 reaction equation
[Cl:1][C:2]1[C:11]([C:12]([C:14]2[CH:15]=[N:16][N:17]([CH2:20][CH3:21])[C:18]=2[OH:19])=[O:13])=[CH:10][C:9]([CH3:22])=[C:8]2[C:3]=1[C:4](=[O:27])[C:5]([CH3:26])([CH3:25])[CH2:6][S:7]2(=[O:24])=[O:23].C(=O)([O-])[O-].[K+].[K+].[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1>O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[Cl:1][C:2]1[C:11]([C:12]([C:14]2[CH:15]=[N:16][N:17]([CH2:20][CH3:21])[C:18]=2[O:19][S:40]([C:37]2[CH:38]=[CH:39][C:34]([CH3:44])=[CH:35][CH:36]=2)(=[O:42])=[O:41])=[O:13])=[CH:10][C:9]([CH3:22])=[C:8]2[C:3]=1[C:4](=[O:27])[C:5]([CH3:26])([CH3:25])[CH2:6][S:7]2(=[O:23])=[O:24]

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 178463107HCID 178463107, compound

Product 1

HCID 22118462HCID 22118462, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

0.60 Gram (1.46 mmol) of 5-chloro-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonyl-3,3,8-trimethylthiochroman-4-one-1,1-dioxide was dissolved in 7 ml of dicholoromethane. Separately, 0.25 g (1.81 mmol) of potassium carbonate was dissolved in 7 ml of water, and these two solutions were mixed. Then, 0.34 g(1.78 mmol) of p-toluenesulfonyl chloride was added. Further, a small amount (about 20 mg) of benzyltriethylammonium chloride was added, and the mixture was stirred at room temperature for about 15 hours. The reaction mixture was diluted with dichloromethane and water and separated into two phases, and an organic layer was washed with diluted hydrochloric acid, then with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and 0.77 g of the resultant oil was purified by silica gel column chromatography (developer solution: n-hexane/ethyl acetate, 2:1 v/v) to give 0.67 g (yield 82% of the titled compound. Table 26 shows the structural formula of the titled compound, and Table 27 shows the physical property data thereof.

Workup

  1. additionthese two solutions were mixed
  2. customseparated into two phases
  3. washan organic layer was washed with diluted hydrochloric acid
  4. dry with materialwith water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure, and 0.77 g of the resultant oil
  6. customwas purified by silica gel column chromatography (developer solution: n-hexane/ethyl acetate, 2:1 v/v)

Sources & evidence

ORD record
ord-1022b73af1544e02abcffa396d054ae2
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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