m-Chloroperbenzoic acid → HCID 21758505, compound

HRID 266438Notes

Reaction equation

HRID 266438 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[N:12]1[CH:17]=[CH:16][CH:15]=[N:14][C:13]=1[S:18][CH2:19][N:20]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[S:21]1(=[O:23])=[O:22]>>[N:14]1[CH:15]=[CH:16][CH:17]=[N:12][C:13]=1[S:18]([CH2:19][N:20]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[S:21]1(=[O:23])=[O:22])=[O:9]

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70052531HCID 70052531, compound

Product 1

HCID 21758505HCID 21758505, compound

Procedure

A mixture of m-chloroperbenzoic acid (0.9 g, 5.37 mmol) and 2-(2-pyrimidylthiomethyl) saccharin prepared by procedures similar to those of Examples 9 and 11 (1.5 g, 4.8 mmol) in MDC (75 ml) was stirred overnight at room temperature. The reaction mixture was washed with sodium bicarbonate solution, dried (Na2SO4) and freed of solvent under vacuum. Part of this crude product (0.5 g) was saved for direct conversion to the sulfone; the remaining material was chromatographed (silica gel-95:5 CH2Cl2 :acetone). Recrystallization from ethanol:acetonitrile afforded 0.95 g of 2-(2-pyrimidylsulfinylmethyl)saccharin as white crystals, mp 197°-198 ° C. decomp. 1H nmr (90 MHz, CDCl3, DMSO-d6) :5.1-5.5 (2H, q) .

Workup

  1. washThe reaction mixture was washed with sodium bicarbonate solution
  2. dry with materialdried (Na2SO4)
  3. customthe remaining material was chromatographed (silica gel-95:5 CH2Cl2 :acetone)
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-86a0c2caba7a4261850bfe3e22347572
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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