Hydrochloric Acid → 1-(4-Methanesulfonylaminophenyl)-3-azabicyclo[3.1.0]hexane-2,4dione

HRID 1904797Notes

Reaction equation

HRID 1904797 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]23[CH2:18][CH:17]2[C:16](=[O:19])[NH:15][C:14]3=[O:20])=[CH:9][CH:8]=1.CN(C1C=CC=CN=1)C.Cl>C(Cl)Cl.O.N1C=CC=CC=1>[CH3:1][S:2]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]23[CH2:18][CH:17]2[C:16](=[O:19])[NH:15][C:14]3=[O:20])=[CH:11][CH:12]=1)(=[O:4])=[O:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 140689341-(4-Aminophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 200380481-(4-Methanesulfonylaminophenyl)-3-azabicyclo[3.1.0]hexane-2,4dione

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.2 ml of methanesulfonyl chloride in 10 ml of methylene chloride is stirred dropwise at room temperature into a mixture of 3 g of 1-(4-aminophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione, 90 mg of dimethylaminopyridine and 37 ml of pyridine. After it has been stirred for 16 hours, the reaction mixture is freed from solvent in vacuo. The residue is dissolved in 100 ml of water and the solution is adjusted to pH 1 with hydrochloric acid. After further stirring, the crystals are isolated by filtration and recrystallised from methanol. The title compound is obtained in the form of whitish orange crystals with a melting point of 208°-209° C. and with Rf=0.32 on thin-layer silica gel plates in the system methylene chloride/methanol (10:1).

Workup

  1. stirringAfter further stirring
  2. customthe crystals are isolated by filtration
  3. customrecrystallised from methanol

Sources & evidence

ORD record
ord-dde90decdc3649e6ade0b9a2e1d3ef3e
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

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