Dichloromethane → HCID 88334468, compound

HRID 1377958Notes

Reaction equation

HRID 1377958 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10](=[O:25])/[C:11](/[C:15]2[N:16]=[C:17]([N:20]=CN(C)C)[S:18][CH:19]=2)=[N:12]\[O:13][CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[Cl-].[NH4+].C(Cl)Cl>CO>[C:1]1([CH2:7][CH2:8][NH:9][C:10](=[O:25])/[C:11](/[C:15]2[N:16]=[C:17]([NH2:20])[S:18][CH:19]=2)=[N:12]\[O:13][CH3:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 140381070HCID 140381070, compound

Product 1

HCID 88334468HCID 88334468, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Z)-N-(2-Phenylethyl)-2-(2-dimethylaminomethylidenaminothiazol-4-yl)-2-methoxyiminoacetamide (130 mg, 0.36 mmol) was dissolved in 4 ml of methanol, followed by the addition of 1 ml of a 1N aqueous solution of sodium hydroxide. The mixture so obtained was stirred at room temperature for 2 days. The reaction mixture was then added with 20 ml of a saturated aqueous solution of ammonium chloride and 20 ml of methylene chloride. The resulting mixture was then allowed to separate into an organic phase and an aqueous phase. The aqueous phase was further extracted twice with 10 ml portions of methylene chloride. All the organic phases were combined, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure, whereby 90 mg of the title compound were obtained (yield: 81.8%).

Workup

  1. customThe mixture so obtained
  2. customto separate into an organic phase
  3. extractionThe aqueous phase was further extracted twice with 10 ml portions of methylene chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e4e5031bdef41f88f7d5542fd86a9c9
Source dataset
uspto-grants-1997_09
Patent number
US05665888

Reaction notes

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