Dimethylformamide → (2Z)-2-[2-(dimethylaminomethylideneamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetyl chloride;hydrochloride

HRID 266247

Reaction equation

HRID 266247 reaction equation
[CH3:1][N:2]([CH3:5])[CH:3]=O.[Cl:6]C([O:9][C:10]([Cl:13])(Cl)Cl)=O.[NH2:14][C:15]1[S:16][CH:17]=[C:18](/[C:20](=[N:24]/[O:25][CH3:26])/C(O)=O)[N:19]=1.C(OC(C)C)(=O)C>O1CCCC1>[ClH:6].[CH3:1][N:2]([CH:3]=[N:14][C:15]1[S:16][CH:17]=[C:18](/[C:20](=[N:24]/[O:25][CH3:26])/[C:10]([Cl:13])=[O:9])[N:19]=1)[CH3:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7915Isopropyl AcetateHCID 10426DiphosgeneHCID 5486924(alphaZ)-2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acid

Product 1

HCID 140382097(2Z)-2-[2-(dimethylaminomethylideneamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetyl chloride;hydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethylformamide (0.8 g, 11 mmol) was added to 9 ml of tetrahydrofuran, followed by ice-cooling. To the resulting mixture, 0.6 ml of trichloromethyl chloroformate was added dropwise under ice-cooling. After stirring the resulting mixture for 30 minutes, the mixture was cooled to -10° C. (Z)-2-(2-Amino-thiazol-4-yl)-2-methoxyiminoacetic acid (840 mg, 4.2 mmol) was added and the mixture so obtained was stirred for 2 hours. The mixture was added with 9 ml of isopropyl acetate, followed by stirring for 30 minutes. A precipitate was collected by filtration under a nitrogen gas stream and then dried at room temperature, whereby 1.23 g of the title compound were obtained (yield: 94%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. additionwas added
  4. customthe mixture so obtained
  5. stirringwas stirred for 2 hours
  6. stirringby stirring for 30 minutes
  7. filtrationA precipitate was collected by filtration under a nitrogen gas stream
  8. customdried at room temperature

Sources & evidence

ORD record
ord-a0f791409a584fea8fb7fb0116e3a933
Source dataset
uspto-grants-1997_07
Patent number
US05650518

Linked notes

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