Potassium Carbonate → HCID 15477817, compound

HRID 1275456Notes

Reaction equation

HRID 1275456 reaction equation
[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:9]([C:11]2[C:12]([CH3:27])=[C:13]3[C:18](=[C:19]([CH3:21])[CH:20]=2)[S:17](=[O:23])(=[O:22])[CH2:16][C:15]([CH3:25])([CH3:24])[C:14]3=[O:26])=[O:10])[CH:5]=[N:4]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:34]([S:37](Cl)(=[O:39])=[O:38])[CH2:35][CH3:36]>ClCCl.O.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[CH2:1]([N:3]1[C:7]([O:8][S:37]([CH2:34][CH2:35][CH3:36])(=[O:39])=[O:38])=[C:6]([C:9]([C:11]2[C:12]([CH3:27])=[C:13]3[C:18](=[C:19]([CH3:21])[CH:20]=2)[S:17](=[O:22])(=[O:23])[CH2:16][C:15]([CH3:24])([CH3:25])[C:14]3=[O:26])=[O:10])[CH:5]=[N:4]1)[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 662791-Propanesulfonyl chlorideHCID 178463104HCID 178463104, compound

Product 1

HCID 15477817HCID 15477817, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent3×

Procedure

2.3 Grams (5.9 mmol) of 6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonyl-3,3,5,8-tetramethylthiochroman-4-one-1,1-dioxide was dissolved in 15 ml of dichloromethane. Separately, 1.22 g (8.8 mmol) of potassium carbonate was dissolved in 20 ml of water, and these two solutions were mixed. Then, a solution of 1.26 g (8.8 mmol) of n-propanesulfonyl chloride in 5 ml of dichloromethane was added. Further, a small amount (about 50 mg) of benzyltrimethylammonium 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 3.02 g of the resultant oil was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate, 2:1 v/v) to give 2.6 g (yield 89%) of the titled compound. Table 25 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 3.02 g of the resultant oil
  6. customwas purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate, 2:1 v/v)

Sources & evidence

ORD record
ord-a8f45231329741c48a8771074e5e8b15
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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