m-Chloroperbenzoic acid → HCID 14996998, compound

HRID 1769716Notes

Reaction equation

HRID 1769716 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][S:13][C:14]1[CH:15]=[C:16]([NH:20][C:21](=[O:46])[NH:22][CH2:23][C:24]([N:26]([CH2:33][C:34](=[O:45])[N:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:38][CH2:37][CH2:36]2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:25])[CH:17]=[CH:18][CH:19]=1>C(Cl)Cl>[CH3:12][S:13]([C:14]1[CH:15]=[C:16]([NH:20][C:21](=[O:46])[NH:22][CH2:23][C:24]([N:26]([CH2:33][C:34](=[O:45])[N:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:38][CH2:37][CH2:36]2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:25])[CH:17]=[CH:18][CH:19]=1)=[O:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14996942HCID 14996942, compound

Product 1

HCID 14996998HCID 14996998, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1.5 g of m-chloroperbenzoic acid in solution in 10 cm3 of methylene chloride is run, in the course of 10 minutes, into a solution of 1.1 g of 2-[3-(3-methylthiophenyl)ureido]-N-[2-oxo-2-(1,2,3,4-tetrahydro-1-quinolyl)ethyl]-N-phenylacetamide in 10 cm3 of methylene chloride kept at a temperature close to 0° C. The mixture is stirred for 2 hours at a temperature close to 25° C and then diluted with 25 cm3 of methylene chloride. The solution is washed with 20 cm3 of a saturated aqueous sodium thiosulphate solution, 20 cm3 of a saturated aqueous sodium bicarbonate solution and then 20 cm3 of a saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The crude product obtained is purified by chromatography on 40 g of silica (0,062-0,200 mm) contained in a column 1.2 cm in diameter [eluent: ethyl acetate/methanol (95/5 by volume)], collecting 10 cm3 fractions. Fractions 6 to 13 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from a diisopropyl ether/ethyl acetate mixture (90/10 by volume), 0.5 g of (RS)-2-[3-(3-methylsulphinylphenyl)ureido]-N-[2-oxo-2-(1,2,3,4-tetrahydro-1-quinolyl)ethyl]-N-phenylacetamide melting at 140° C is obtained.

Workup

  1. customclose to 0° C
  2. customclose to 25° C
  3. washThe solution is washed with 20 cm3 of a saturated aqueous sodium thiosulphate solution, 20 cm3 of a saturated aqueous sodium bicarbonate solution
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  6. customThe crude product obtained
  7. customis purified by chromatography on 40 g of silica (0,062-0,200 mm)
  8. customcollecting 10 cm3 fractions
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  10. customAfter recrystallization from a diisopropyl ether/ethyl acetate mixture (90/10 by volume)

Sources & evidence

ORD record
ord-3f34c52afd49413e83b94694ca57c0d5
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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