Dichloromethane → HCID 178515056, compound

HRID 266436Notes

Reaction equation

HRID 266436 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]1([CH:18]([S:31][C:32]2[NH:36][N:35]=[N:34][N:33]=2)[N:19]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[S:20]2(=[O:22])=[O:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(Cl)Cl>CCOCC>[C:12]1([CH:18]([S:31]([C:32]2[NH:36][N:35]=[N:34][N:33]=2)=[O:9])[N:19]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[S:20]2(=[O:22])=[O:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 178515059HCID 178515059, compound

Product 1

HCID 178515056HCID 178515056, compoundYield 199.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of m-chloroperbenzoic acid (0.43 g, 9,.67 mmol) and 2-(1-phenyl-1H-tetrazol-5-ylthiomethyl) saccharin (1 g, 2.67 mmol) in MDC was stirred at room temperature for 24 hours. TLC (95:5 CH2Cl2 : ether) revealed the presence of starting sulfide. Additional peracid (0.2 g) was added and the mixture stirred for an additional 2 days. The reaction mixture was washed with sodium bicarbonate solution, dried (Na2SO4) and freed of solvent under vacuum. Chromatography (silica gel-95:5 CH2Cl2 :ether) afforded a foam that was crystallized from ether to afford 0.52 g of 2-(1-phenyl-1H-tetrazol-5-ylsulfinylmethyl) saccharin as a white solid, mp 161°-162° C. 1H nmr (90 MHz, CDCl3):5.5-6.0 (2H, q). FDMS: m/e 196 (M+ -PMT), 389 (M+).

Workup

  1. stirringthe mixture stirred for an additional 2 days
  2. washThe reaction mixture was washed with sodium bicarbonate solution
  3. dry with materialdried (Na2SO4)
  4. customChromatography (silica gel-95:5 CH2Cl2 :ether) afforded a foam that
  5. customwas crystallized from ether

Sources & evidence

ORD record
ord-3b93cfad4b354378b3663a39b36bdf6a
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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