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Sodium Thiosulfate → 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[(phenylsulfinyl)acetyl]hydrazide

HRID 2119045
Notes
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Reaction equation

HRID 2119045 reaction equation
[C:1]1([S:7][CH2:8][C:9]([NH:11][NH:12][C:13]([N:15]2[CH2:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[O:18][C:17]3[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:16]2=3)=[O:14])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:36].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[C:1]1([S:7]([CH2:8][C:9]([NH:11][NH:12][C:13]([N:15]2[CH2:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[O:18][C:17]3[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:16]2=3)=[O:14])=[O:10])=[O:36])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 139213678-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[(phenylthio)acetyl]hydrazide

Product 1

HCID 139874318-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[(phenylsulfinyl)acetyl]hydrazide

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a stirred solution of 1.0 g (2.19 mmole) of the title product of Example 2 in 30 ml of cold (ca. 0°) dichloromethane was added 0.463 g (2.19 mmole) of 81% m-chloroperoxybenzoic acid. After about ninety minutes, 5 ml of saturated aqueous sodium thiosulfate was added. The mixture was washed sequentially with three portions of saturated aqueous sodium bicarbonate and three portions of water. The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo to give tht title compound.

Workup

  1. waitAfter about ninety minutes
  2. washThe mixture was washed sequentially with three portions of saturated aqueous sodium bicarbonate and three portions of water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac374aa439cc4f81b12b320a3cde3e40
Source dataset
uspto-grants-1987_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04681939

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes