Cesium carbonate → N-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-1,1-dioxo-1,2-benzothiazol-3-amine

HRID 277136Notes

Reaction equation

HRID 277136 reaction equation
[S:1]1(=[O:12])(=[O:11])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH2:10])=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[CH:24]1[CH2:27][N:26]([CH:28]([C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=2)[C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[CH2:25]1)(=O)=O>CN(C)C=O>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([CH:28]([C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)[N:26]2[CH2:27][CH:24]([NH:10][C:3]3[C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=4[S:1](=[O:11])(=[O:12])[N:2]=3)[CH2:25]2)=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 647861,2-Benzisothiazol-3-amine 1,1-dioxideHCID 218966031-[Bis(4-chlorophenyl)methyl]azetidin-3-yl methylsulfonate

Product 1

HCID 178527183N-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-1,1-dioxo-1,2-benzothiazol-3-amineYield 11.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

182 mg of 1,2-benzisothiazol-3-amine 1,1-dioxide and 326 mg of cesium carbonate are added to 386 mg of 1-[bis(4-chlorophenyl)methyl]azetidin-3-yl methylsulfonate in solution in 10 cm3 of dimethylformamide. The reaction medium is then stirred at 100° C. for 9 hours and then concentrated under reduced pressure (2.7 kPa). The residue is washed four times with 5 cm3 of boiling distilled water, disintegrated by stirring in 5 cm3 of distilled water at room temperature and then recovered by filtration and purified by flash chromatography on silica gel [eluent: dichloromethane/methanol (98/2 by volume)]. 53 mg of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-(1,1-dioxo-1H-1λ6-benzo[d]isothiazol-3-yl)amine are obtained in the form of a pasty product [[1H NMR spectrum (300 MHz, CDCl3, δ in ppm): 3.17 (mt: 2H); 3.61 (broad t, J=7.5 Hz: 2H); 4.37 (s: 1H); 4.75 (mt: 1H); from 6.30 to 6.40 (unresolved complex: 1H); from 7.20 to 7.35 (mt: 8H); 7.62 (broad d, J=7.5 Hz: 1H); 7.69 (broad t, J=7.5 Hz: 1H); 7.76 (broad t, J=7.5 Hz: 1H); 7.93 (broad d, J=7.5 Hz: 1H)].

Workup

  1. concentrationconcentrated under reduced pressure (2.7 kPa)
  2. washThe residue is washed four times with 5 cm3
  3. distillationof boiling distilled water
  4. stirringby stirring in 5 cm3 of distilled water at room temperature
  5. filtrationrecovered by filtration
  6. custompurified by flash chromatography on silica gel [eluent: dichloromethane/methanol (98/2 by volume)]

Sources & evidence

ORD record
ord-17e72a086de541f9bfa83e93985d843d
Source dataset
uspto-grants-2002_03
Patent number
US06355631B1

Reaction notes

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