4-Toluenesulfonyl chloride → HCID 10712489, compound

HRID 654068Notes

Reaction equation

HRID 654068 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH:12]1[C:21]2[N:20]3[CH:22]=[CH:23][CH:24]=[C:19]3[CH2:18][NH:17][CH2:16][C:15]=2[S:14][CH:13]=1>N1C=CC=CC=1.O>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([N:17]2[CH2:16][C:15]3[S:14][CH:13]=[CH:12][C:21]=3[N:20]3[CH:22]=[CH:23][CH:24]=[C:19]3[CH2:18]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 10655302HCID 10655302, compound

Product 1

HCID 10712489HCID 10712489, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

An excess of para-toluenesulfonyl chloride is added to a solution of 1 g (0.0053 mol) of 5,6-dihydro -4H-pyrrolo[1,2-a]thieno[2,3-f][1,4]diazepine in 10 ml of pyridine, and the reaction mixture is then stirred at room temperature for one hour. The pyridine is then removed under reduced pressure and the oil residue obtained is ground in 100 ml of water. The emulsion formed is extracted with 3 times 100 ml of ethyl ether. The organic phases are separated after settling has taken place, combined, dried, washed with acidulated water, dried over magnesium sulfate and evaporated under vacuum. The solid residue is recrystallized. 0.4 g of 5-(p-tolylsulfonyl)-5,6-dihydro-4H -pyrrolo[1,2-a]thieno[2,3-f][1,4]diazepine is thereby obtained in the form of yellow crystals, melting point 165° C. (ethyl ether).

Workup

  1. customThe pyridine is then removed under reduced pressure
  2. customthe oil residue obtained
  3. customThe emulsion formed
  4. extractionis extracted with 3 times 100 ml of ethyl ether
  5. customThe organic phases are separated after settling
  6. customdried
  7. washwashed with acidulated water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under vacuum
  10. customThe solid residue is recrystallized

Sources & evidence

ORD record
ord-cc1d3aed32884c959709e3fb18070deb
Source dataset
uspto-grants-1992_07
Patent number
US05130301

Reaction notes

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