Benzenesulfonyl chloride → HCID 18981105, compound

HRID 482447Notes

Reaction equation

HRID 482447 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:21]=[C:20]2[C:15]([C:16](=[O:38])[N:17]([CH3:37])[C:18]([C:22]3[CH:36]=[CH:35][C:25]([CH2:26][P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])=[CH:24][CH:23]=3)=[N:19]2)=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH3:37][N:17]1[C:16](=[O:38])[C:15]2[C:20](=[CH:21][C:12]([NH:11][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])=[CH:13][CH:14]=2)[N:19]=[C:18]1[C:22]1[CH:23]=[CH:24][C:25]([CH2:26][P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 18981120HCID 18981120, compound

Product 1

HCID 18981105HCID 18981105, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzenesulfonyl chloride (0.57 ml) was slowly added dropwise at 0° C. to 10 ml of pyridine containing 1.5 g of the compound obtained in Example 66. The mixture was stirred at room temperature for 12 hours. After adding a saturated sodium bicarbonate solution, the reaction mixture was extracted with dichloromethane. The organic layer was washed with diluted hydrochloric acid, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from diethyl ether to give 1.75 g of the desired compound as colorless crystals. Table 3 shows the chemical structure and physical property (melting point) of the compound obtained.

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. washThe organic layer was washed with diluted hydrochloric acid
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-98637decdb4b49b6862df092579e1d0c
Source dataset
uspto-grants-1998_08
Patent number
US05798344

Reaction notes

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