m-Chloroperbenzoic acid → HCID 54710173, compound

HRID 1080652Notes

Reaction equation

HRID 1080652 reaction equation
[CH3:1][N:2]([C:20]1[CH:25]=[CH:24][C:23]([S:26][CH3:27])=[CH:22][CH:21]=1)[C:3]([C:5]1[C:17](=[O:18])[N:13]2[CH2:14][CH2:15][O:16][C:11]3[C:12]2=[C:7]([CH:8]=[CH:9][CH:10]=3)[C:6]=1[OH:19])=[O:4].ClC1C=CC=C(C(OO)=[O:36])C=1>ClCCl>[CH3:1][N:2]([C:20]1[CH:21]=[CH:22][C:23]([S:26]([CH3:27])=[O:36])=[CH:24][CH:25]=1)[C:3]([C:5]1[C:17](=[O:18])[N:13]2[CH2:14][CH2:15][O:16][C:11]3[C:12]2=[C:7]([CH:8]=[CH:9][CH:10]=3)[C:6]=1[OH:19])=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54710161HCID 54710161, compound

Product 1

HCID 54710173HCID 54710173, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 6-[N-methyl-N-(4-methylthiophenyl)carbamoyl]-2,3-dihydro-7-hydroxy-5-oxo-5H-pyrido-[1,2,3-de]-1,4-benzoxazine (1 g) and m-chloroperbenzoic acid (0.5 g) in dichloromethane (50 ml) was stirred at 5° C. for 1 hour. The insoluble material was filtered and the filtrate was concentrated in vacuo. The residue was recrystallized from acetone to give pale brown crystals of 6-[N-methyl-N-(4-methylsulfinylphenyl)carbamoyl]-2,3-dihydro-7-hydroxy-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (0.82 g).

Workup

  1. filtrationThe insoluble material was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-0fdffd11d6454ecdadfcb5a7e726e793
Source dataset
uspto-grants-1996_12
Patent number
US05583135

Reaction notes

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