m-Chloroperbenzoic acid → HCID 178502524, compound

HRID 847733Notes

Reaction equation

HRID 847733 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([S:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH:8]=[CH:7][C:6]=1[NH:16][C:17](=[N:23][C:24](=[O:27])[O:25][CH3:26])[NH:18][C:19]([O:21][CH3:22])=[O:20])(=[O:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:33]>C(Cl)(Cl)Cl>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([S:11]([CH2:12][CH:13]([CH3:15])[CH3:14])=[O:33])[CH:8]=[CH:7][C:6]=1[NH:16][C:17](=[N:18][C:19](=[O:20])[O:21][CH3:22])[NH:23][C:24]([O:25][CH3:26])=[O:27])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178502522HCID 178502522, compound

Product 1

HCID 178502524HCID 178502524, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 3.9 g (0.01 mole) of [[[2-(acetylamino)-4-[(2-methylpropyl)thio]phenyl]amino][(methoxycarbonyl)amino]methylene carbamic acid, methyl ester in 250 ml of chloroform there is added 2.0 g (0.01 mole of 85% m-chloroperoxybenzoic acid in 10 ml of chloroform with ice bath cooling. The reaction mixture is allowed to warm to room temperature and then stirred for 3 hours. The reaction mixture is washed with aqueous potassium carbonate and then with water until the pH is 7. The organic layer is dried (MgSO4), filtered, and evaporated in vacuo. The residue is crystallized from ethanol to yield 1.8 g, m.p. 178°-180° C. dec.

Workup

  1. temperaturecooling
  2. washThe reaction mixture is washed with aqueous potassium carbonate
  3. dry with materialThe organic layer is dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue is crystallized from ethanol
  7. customto yield 1.8 g, m.p. 178°-180° C. dec.

Sources & evidence

ORD record
ord-94a1cbc4273a469f99b7afa7421a2294
Source dataset
uspto-grants-1981_10
Patent number
US04293569

Reaction notes

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