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Hydroxyamine hydrochloride → 2-(1-Benzyl-5-methyl-4-imidazolyl)-1,3-dithian-5-one oxime

HRID 27178
Notes
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Reaction equation

HRID 27178 reaction equation
[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([CH:14]2[S:19][CH2:18][C:17](=O)[CH2:16][S:15]2)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].Cl.[NH2:27][OH:28]>CO.O.C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([CH:14]2[S:19][CH2:18][C:17](=[N:27][OH:28])[CH2:16][S:15]2)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 233436742-(1-Benzyl-5-methyl-4-imidazolyl)-1,3-dithian-5-one

Product 1

HCID 233436822-(1-Benzyl-5-methyl-4-imidazolyl)-1,3-dithian-5-one oximeYield 94.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent
HCID 962
Water
Solvent
HCID 6212ChloroformSolvent

Procedure

To a solution of 2-(1-benzyl-5-methyl-4-imidazolyl)-1,3-dithian-5-one (11.2 g., 0.0368 mole) in methanol (50 ml.) and water (20 ml.) is added sodium acetate (3.1 g.) and hydroxylamine hydrochloride (2.6 g., 0.037 mole). The reaction is stirred at ambient temperature for 5 hours. The mixture is diluted with chloroform, washed with water, dried and evaporated to give a solid crude product (11.1 g.), 2-(1-benzyl-5-methyl-4-imidazolyl)-1,3-dithian-5-one oxime, which is used as is in the following steps.

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-b3c919a875bd4fe081611d6c5b47ff54
Source dataset
uspto-grants-1980_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04220654

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes