Nitrogen → HCID 178504156, compound

HRID 1078703Notes

Reaction equation

HRID 1078703 reaction equation
N#N.C[S:4]([C:7]1[CH:12]=[CH:11][CH:10]=CC=1)(=O)=O.[C:13]1([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:26]S(O)(=O)=O.[Cl:31]([OH:35])(=[O:34])(=[O:33])=[O:32].[OH2:36]>ClCCl>[Cl:31]([O-:35])(=[O:34])(=[O:33])=[O:32].[CH3:26][SH+:19]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([O:36][C:12]1[CH:11]=[CH:10][S:4][CH:7]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

8

Reactant 6

HCID 947NitrogenHCID 962WaterHCID 6395Methanesulfonic AcidHCID 8766Diphenyl sulfideHCID 18369Methyl phenyl sulfoneHCID 24247Perchloric Acid

Product 1

HCID 178504156HCID 178504156, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 300-mL, three-neck, round-bottom flask, which has a thermometer and N2 gas inlet and is equipped with a Teflon-covered magnetic stirring bar, is charged with methylphenylsulfone (7 g, 50 mmol) and diphenylsulfide (9.3 g, 50 mmol). The reaction mixture is cooled to 0° C. Methanesulfonic acid (100 mL) is added to the reaction vessel. The temperature is gradually raised to room temperature over a 30-min period. The reaction is continued for 20 h at room temperature. The reaction mixture is then poured into perchloric acid (60%, 100 mL) and stirred for 1 h at room temperature, and then water (100 mL) and dichloromethane (100 mL) were added. The aqueous layer is extracted with dichloromethane (2×50 mL). The organic layer is dried over anhydrous sodium sulfate. After evaporation, a residue is purified by recrystallization with ether. The solid is dried under vacuum at room temperature for 20 h.

Workup

  1. temperatureThe temperature is gradually raised to room temperature over a 30-min period
  2. extractionThe aqueous layer is extracted with dichloromethane (2×50 mL)
  3. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  4. customAfter evaporation
  5. customa residue is purified by recrystallization with ether
  6. customThe solid is dried under vacuum at room temperature for 20 h.

Sources & evidence

ORD record
ord-88637daaf187428b96829e680a79a71e
Source dataset
uspto-grants-1996_08
Patent number
US05550171

Reaction notes

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