Benzene → HCID 15291091, compound

HRID 128702

Reaction equation

HRID 128702 reaction equation
C1OCCOCCOCCOCCOCCOC1.C1C=CC=CC=1.Cl[CH2:26][N:27]1[C:37](=[O:38])[C:36]2[C:31](=[CH:32][C:33]([O:42][CH3:43])=[CH:34][C:35]=2[CH:39]([CH3:41])[CH3:40])[S:28]1(=[O:30])=[O:29].[N-:44]=[N+:45]=[N-:46].[Na+]>O>[N:44]([CH2:26][N:27]1[C:37](=[O:38])[C:36]2[C:31](=[CH:32][C:33]([O:42][CH3:43])=[CH:34][C:35]=2[CH:39]([CH3:41])[CH3:40])[S:28]1(=[O:30])=[O:29])=[N+:45]=[N-:46]

Participants

6

Reactant 4

HCID 241BenzeneHCID 2855718-Crown-6HCID 33557Sodium AzideHCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 15291091HCID 15291091, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 18-crown-6 ether (0.60 g) and benzene (60 mL) was heated under reflux with a water separator for 1 hour, then cooled to room temperature. 2-Chloromethyl-4-isopropyl-6-methoxysaccharin (3.03 g) and sodium azide (0.65 g) were added, and the mixture was stirred for a week at room temperature, then chromatographed on a column of silica gel (silica gel 60, 83 g) using benzene as eluant. The fractions containing the product, which were identified by thin layer chromatography, were combined and concentrated affording 2-azidomethyl-4-isopropyl-6-methoxysaccharin as a solution in benzene (250 mL).

Workup

  1. customchromatographed on a column of silica gel (silica gel 60, 83 g)
  2. additionThe fractions containing the product, which
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1d4838076b604dfe911e87f95da97d89
Source dataset
uspto-grants-1995_11
Patent number
US05464852

Linked notes

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