m-Chloroperbenzoic acid → 20290-48-6

HRID 974803Notes

Reaction equation

HRID 974803 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH:12]1[C:17]2[C:18](=[O:27])[NH:19][C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=3[S:22][C:16]=2[CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH:12]1[C:17]2[C:18](=[O:27])[NH:19][C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=3[S:22](=[O:9])[C:16]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 374829DibenzothiazepinoneHCID 516892Sodium Bicarbonate

Product 1

HCID 1300037220290-48-6

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of MCPBA (1 eq) in chloroform (5 ml) was added to a stirred solution of 10,11-dihydrodibenzo[b,f][1,4] thiazepin-11-one (114 mg, 0.5 mmol) in chloroform (30 ml). After 0.5 hr the reaction mixture was poured into sodium bicarbonate solution (5%, 30 ml), separated and the aqueous layer washed with chloroform (30 ml). The combined organic fractions were dried (MgSO4) and evaporated. Recrystallisation from toluene gave the title compound as off-white crystals (76 mg, m.p. 308°-310° C., Rf 0.16, CH2Cl2 /MeOH 50:1).

Workup

  1. customseparated
  2. washthe aqueous layer washed with chloroform (30 ml)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. customevaporated
  5. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-591f3b49902d4942af36c3b9b0e0f97d
Source dataset
uspto-grants-1997_03
Patent number
US05607929

Reaction notes

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