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Phenethylamine → N-(2-phenylethyl)-2-(2-dimethylaminomethylidenaminothiazol-4-yl)-2-methoxyiminoacetamide

HRID 266252
Notes
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Reaction equation

HRID 266252 reaction equation
[Cl-].CN([NH+]=CCl)C.Cl.[NH2:9][C:10]1[S:11][CH:12]=[C:13](/[C:15](=[N:19]/[O:20][CH3:21])/[C:16](Cl)=[O:17])[N:14]=1.[CH2:22]([N:24]([CH2:27]C)[CH2:25]C)C.[CH:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][NH2:37])=[CH:31][CH:30]=1>O1CCCC1.O>[C:32]1([CH2:35][CH2:36][NH:37][C:16](=[O:17])[C:15]([C:13]2[N:14]=[C:10]([N:9]=[CH:27][N:24]([CH3:22])[CH3:25])[S:11][CH:12]=2)=[N:19][O:20][CH3:21])[CH:33]=[CH:34][CH:29]=[CH:30][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 10131288(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl chloride hydrochlorideHCID 86750850Dimethylaminochloromethyleneammonium chloride

Product 1

HCID 57292777N-(2-phenylethyl)-2-(2-dimethylaminomethylidenaminothiazol-4-yl)-2-methoxyiminoacetamideYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Dimethylaminochloromethyleneammonium chloride (430 mg, 3.36 mmol) was dissolved in 15 ml of tetrahydrofuran. Added to the solution were 860 mg (3.36 mmol) of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetyl chloride hydrochloride, followed by stirring at room temperature for 1 hour. To the solution so obtained, a solution of 1.02 g (10.1 mmol) of triethylamine and 0.35 g (2.9 mmol) of β-phenethylamine in 4 ml of tetrahydrofuran was added. The mixture so obtained was stirred for 2 hours under ice-cooling and further for 15 hours at room temperature. The reaction mixture was added with 100 ml of water and then extracted three times with 50 ml portions of chloroform. The organic phases were combined, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue so obtained was purified by chromatography on a silica gel column, whereby 0.98 g of the title compound was obtained (yield: 95%).

Workup

  1. additionAdded to the solution
  2. customTo the solution so obtained
  3. customThe mixture so obtained
  4. stirringwas stirred for 2 hours under ice-
  5. temperaturecooling and further for 15 hours at room temperature
  6. extractionextracted three times with 50 ml portions of chloroform
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue so obtained
  10. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-6e3c02a1dde8401ba486d619c5b65a2f
Source dataset
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05650518

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes