Dimethyl Sulfide → HCID 68662228, compound

HRID 729330Notes

Reaction equation

HRID 729330 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:17](=[O:33])[N:18]([C:29]([CH3:32])([CH3:31])[CH3:30])[S:19](=[O:28])(=[O:27])[C:20]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.B(F)(F)F.CCOCC.CSC>C(Cl)Cl>[C:29]([N:18]1[C:17](=[O:33])[C:16]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)=[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:19]1(=[O:27])=[O:28])([CH3:32])([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 8000Boron trifluoride etherateHCID 68661654HCID 68661654, compound

Product 1

HCID 68662228HCID 68662228, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{[4-(Benzyloxy)phenyl]amino}-2-tert-butyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.330 g, 0.71 mmol) was dissolved in dry DCM (40 ml). Boron trifluoride diethyl etherate (1.01 g, 7.13 mmol) and dimethyl sulfide (0.443 g, 7.13 mmol) were added and the reaction mixture was stirred at rt for 41 h. The solvent was evaporated and the residue was dissolved in EtOAc (150 ml) The mixture was washed with water (200 ml), dried (MgSO4), filtered and evaporated. The residue was purified by silica gel column chromatography using a heptane and EtOAc (70:30) as eluant to give the title compound (0.111 g, 42%). 1H NMR (500 MHz, CD3OD): δ 7.21-7.16 (m, 1H), 7.13-7.05 (m 4H), 6.63-6.59 (m, 2H), 6.40-6.36 (m, 2H), 1.74 (s, 9H); 13C NMR (125 MHz, CD3OD): δ 161.2, 155.9, 133.9, 130.7, 130.2, 129.5, 128.8, 126.8, 125.5, 115.7, 62.3, 27.9; Mass Spectrum: M+H+ 373.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc (150 ml) The mixture
  3. washwas washed with water (200 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2fb13e2d25844816b23b19a87a0d7e33
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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