m-Chloroperbenzoic acid → HCID 53723521, compound

HRID 1382997Notes

Reaction equation

HRID 1382997 reaction equation
[CH3:1][N:2]([CH3:18])[CH:3]=[N:4][S:5]([C:8]1[O:16][C:15]2[CH:14]=[C:13]([CH3:17])[N:12]=[CH:11][C:10]=2[CH:9]=1)(=[O:7])=[O:6].ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:18])[CH:3]=[N:4][S:5]([C:8]1[O:16][C:15]2[CH:14]=[C:13]([CH3:17])[N+:12]([O-:27])=[CH:11][C:10]=2[CH:9]=1)(=[O:6])=[O:7]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54369360HCID 54369360, compound

Product 1

HCID 53723521HCID 53723521, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of N,N-dimethyl-N'-(6-methylfuro[3.2-c]pyridine-2-sulfonyl)formamidine (5.61 g, 21 mmol) in chloroform (65 ml) was added dropwise a solution of commercial 80% pure m-chloroperbenzoic acid (5.0 g, 23 mmol) in chloroform (45 ml). The reaction was stirred for 20 hours and then concentrated on a rotary evaporator to near dryness. The residue was digested in diethyl ether and the precipitated product filtered. This solid (6.06 g) was digested in ethyl acetate/chloroform/methanol and then cooled and pure product collected by filtration (5.76 g, 97% yield), m.p. 248°-249° C.

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. filtrationthe precipitated product filtered
  3. temperaturecooled
  4. filtrationpure product collected by filtration (5.76 g, 97% yield), m.p. 248°-249° C.

Sources & evidence

ORD record
ord-a29de384a91b4deba55962b1a5746530
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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