m-Chloroperbenzoic acid → HCID 54734235, compound

HRID 1080644Notes

Reaction equation

HRID 1080644 reaction equation
[OH:1][C:2]1[C:11]2[CH:12]=[C:13]([O:15][CH3:16])[CH:14]=[C:9]3[C:10]=2[N:5]([CH2:6][CH2:7][S:8]3)[C:4](=[O:17])[C:3]=1[C:18](=[O:27])[N:19]([CH3:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.ClC1C=C(C=CC=1)C(OO)=[O:33]>ClCCl>[OH:1][C:2]1[C:11]2[CH:12]=[C:13]([O:15][CH3:16])[CH:14]=[C:9]3[C:10]=2[N:5]([CH2:6][CH2:7][S:8]3=[O:33])[C:4](=[O:17])[C:3]=1[C:18](=[O:27])[N:19]([CH3:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54710187HCID 54710187, compound

Product 1

HCID 54734235HCID 54734235, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 2,3-dihydro-7-hydroxy-9-methoxy-6-(N-methyl-N-phenylcarbamoyl)-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzothiazine (1 g) and m-chloroperoxybenzoic 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 (1.5 g) was recrystallized from acetone to give pale yellow crystals of 2,3-dihydro-7-hydroxy-9-methoxy-6-(N-methyl-N-phenylcarbamoyl)-5-oxo-5H-pyrido[1,2,3-de]-1,4benzothiazine 1-oxide (0.86 g).

Workup

  1. filtrationThe insoluble material was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue (1.5 g) was recrystallized from acetone

Sources & evidence

ORD record
ord-c1a501059132443194192cf5276637e4
Source dataset
uspto-grants-1996_12
Patent number
US05583135

Reaction notes

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