m-Chloroperbenzoic acid → HCID 59743399, compound

HRID 1946995Notes

Reaction equation

HRID 1946995 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][S:13][C:14]1[N:19]=[C:18]([N:20]2[C:28]3[C:23](=[C:24]([N+:29]([O-:31])=[O:30])[CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21]2)[CH:17]=[CH:16][N:15]=1>C(Cl)(Cl)Cl.C(Cl)Cl>[CH3:12][S:13]([C:14]1[N:19]=[C:18]([N:20]2[C:28]3[C:23](=[C:24]([N+:29]([O-:31])=[O:30])[CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21]2)[CH:17]=[CH:16][N:15]=1)=[O:6]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59743448HCID 59743448, compound

Product 1

HCID 59743399HCID 59743399, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A suspension of 3-chloroperoxybenzoic acid (77%, 3.11 g) in CHCl3 (40 mL) was slowly added at 0° C. under N2 to a mixture of 1-(2-methylsulfanylpyrimidin-4-yl)-4-nitro-1H-indole (3.93 g, 14.0 mmol) in CHCl3 (50 mL). The resulting mixture was allowed to warm up to RT, and stirred overnight. The reaction mixture was then diluted with DCM (200 mL) and washed with aqueous NaHCO3 (saturated). The resulting yellow precipitate was collected by filtration and dried under reduced pressure to give 1-(2-methanesulfinyl-pyrimidin-4-yl)-4-nitro-1H-indole (2.36 g). The mother liquors were dried over Na2SO4, filtered and evaporated under reduced pressure to give a second aliquot (690 mg).

Workup

  1. washwashed with aqueous NaHCO3 (saturated)
  2. filtrationThe resulting yellow precipitate was collected by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-10c1f5864a414572a02ec046da1dfa0e
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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