m-Chloroperbenzoic acid → HCID 12959732, compound

HRID 1065192Notes

Reaction equation

HRID 1065192 reaction equation
[CH2:1]([S:3][CH2:4][CH2:5][NH:6][C:7](=[O:25])[C:8]1[CH2:24][CH2:23][CH2:22][CH2:21][C:9]=1[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[F:20])=[O:11])[CH3:2].ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)(Cl)Cl>[CH2:1]([S:3]([CH2:4][CH2:5][NH:6][C:7](=[O:25])[C:8]1[CH2:24][CH2:23][CH2:22][CH2:21][C:9]=1[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[F:20])=[O:11])=[O:34])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12959726HCID 12959726, compound

Product 1

HCID 12959732HCID 12959732, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In chloroform (30 ml) was dissolved N-(2-ethylthioethyl)-N'-(2-fluoro-4-chlorophenyl)-3,4,5,6-tetrahydrophthalamide (1.9 g), and with stirring at a constant temperature of 3°-8° C. m-Chloroperbenzoic acid (1.0 g) was added in small portions over an hour. The mixture was stirred at the same temperature for 3 hours and, then, allowed to stand at room temperature overnight. The solution was washed twice with a 10% aqueous solution of sodium nitrite (20 ml each), washed with water and dried over anhydrous sodium sulfate. The chloroform layer was concentrated to dryness under reduced pressure and the residue was recrystallized from ethyl acetate. Yield 1.8 g; m.p. 136°-137° C.

Workup

  1. additionwas added in small portions over an hour
  2. waitto stand at room temperature overnight
  3. washThe solution was washed twice with a 10% aqueous solution of sodium nitrite (20 ml each)
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe chloroform layer was concentrated to dryness under reduced pressure
  7. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1cab72dd65594877bbd51c0fb7b9b82a
Source dataset
uspto-grants-1982_05
Patent number
US04328367

Reaction notes

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