m-Chloroperbenzoic acid → N,N-dimethyl-N'-(6-oxido-thieno[2,3-c]pyridine-2-sulfonyl)formamidine

HRID 569053Notes

Reaction equation

HRID 569053 reaction equation
[CH3:1][N:2]([CH3:17])[CH:3]=[N:4][S:5]([C:8]1[S:16][C:11]2=[CH:12][N:13]=[CH:14][CH:15]=[C:10]2[CH:9]=1)(=[O:7])=[O:6].ClC1C=CC=C(C(OO)=[O:26])C=1>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:1][N:2]([CH3:17])[CH:3]=[N:4][S:5]([C:8]1[S:16][C:11]2=[CH:12][N+:13]([O-:26])=[CH:14][CH:15]=[C:10]2[CH:9]=1)(=[O:6])=[O:7]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54324967N,N-Dimethyl-N'-(thieno[2,3-c]pyridine-2-sulfonyl)formamidine

Product 1

HCID 54087375N,N-dimethyl-N'-(6-oxido-thieno[2,3-c]pyridine-2-sulfonyl)formamidineYield 91.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N,N-dimethyl-N'-(thieno[2,3-c]pyridine-2-sulfonyl)formamidine (2.05 g, 7.6 mmol) in chloroform (30 ml) was added dropwise a solution of m-chloroperbenzoic acid (1.82 g, 8.5 mmol) in ethyl acetate (17 ml). After stirring at room temperature for 18 hours, the precipitated product was collected on a filter. The filtrate was concentrated to obtain additional product. The combined material (2.08 g) was crystallized from chloroform to give 1.98 g (91% yield) of pure product; m.p. 237°-239° C.

Workup

  1. customthe precipitated product was collected on a filter
  2. concentrationThe filtrate was concentrated
  3. customto obtain additional product
  4. customThe combined material (2.08 g) was crystallized from chloroform

Sources & evidence

ORD record
ord-790e15884a8b4e6caec46c1452bd911d
Source dataset
uspto-grants-1988_03
Patent number
US04731368

Reaction notes

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