4-Nitrobenzenesulfonyl chloride → HCID 54556373, compound

HRID 1292502Notes

Reaction equation

HRID 1292502 reaction equation
[CH3:1][O:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:14]([C:16]3[CH:17]=[N:18][N:19]([CH2:22][CH3:23])[C:20]=3[OH:21])=[O:15])[C:11]=2[CH3:13])[S:6](=[O:25])(=[O:24])[CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[N+:32]([C:35]1[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1)([O-:34])=[O:33].[Cl-].ClCC[N+](CC1C=CC=CC=1)(CC)CC>C(Cl)Cl.O>[CH3:1][O:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:14]([C:16]3[CH:17]=[N:18][N:19]([CH2:22][CH3:23])[C:20]=3[O:21][S:41]([C:38]3[CH:37]=[CH:36][C:35]([N+:32]([O-:34])=[O:33])=[CH:40][CH:39]=3)(=[O:42])=[O:43])=[O:15])[C:11]=2[CH3:13])[S:6](=[O:24])(=[O:25])[CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 86752662HCID 86752662, compoundHCID 178418308HCID 178418308, compound

Product 1

HCID 54556373HCID 54556373, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Methoxy-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl) carbonylthiochroman-1,1-dioxide was used as a starting material (XIH). And, 0.4 g (1.10 mmol) thereof was dissolved in 6 ml of methylene chloride, a solution of 0.30 g (2.20 mmol) of potassium carbonate as a base in 4 ml of water was added, and 0.29 g (1.30 mmol) of p-nitrobenzenesulfonyl chloride and 0.05 g (0.2 mmol) of chlorobenzyltriethylammonium chloride as reaction reagents (XII) were added. The resultant mixture was allowed to react at room temperature for 2 hours. Further, the reaction mixture was refluxed under heat for 2 hours. After the reaction mixture was allowed to cool, its methylene chloride layer was separated, and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the resultant oil was purified with flush column chromatography to give 0.42 g (yield 70%) of 4-methoxy-5-methyl-6-(1-ethyl-5-(p-nitrobenzenesulfonyl) oxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound No. 13) as an end compound which comes under the general formula (XI). Table 22 shows the structures of the starting material (XIH) and the reaction reagent (XII), and the structure and the yield of the end product (XI).

Workup

  1. additionwere added
  2. customto react at room temperature for 2 hours
  3. temperatureFurther, the reaction mixture was refluxed
  4. temperatureunder heat for 2 hours
  5. temperatureto cool
  6. customits methylene chloride layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThen, the solvent was distilled off under reduced pressure
  9. customthe resultant oil was purified
  10. customwith flush column chromatography

Sources & evidence

ORD record
ord-f466f0ba3e8f4966a881aa268c7a4419
Source dataset
uspto-grants-1998_05
Patent number
US05756759

Reaction notes

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