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

HRID 266246

Reaction equation

[CH3:1][N:2]([CH3:5])[CH:3]=O.C(Cl)(=O)C([Cl:9])=O.[NH2:12][C:13]1[S:14][CH:15]=[C:16](/[C:18](=[N:22]/[O:23][CH3:24])/[C:19](O)=[O:20])[N:17]=1>O1CCCC1>[ClH:9].[CH3:1][N:2]([CH:3]=[N:12][C:13]1[S:14][CH:15]=[C:16](/[C:18](=[N:22]/[O:23][CH3:24])/[C:19]([Cl:9])=[O:20])[N:17]=1)[CH3:5]

Participants

Conditions

Temperature: -15 °C

Procedure

Dimethylformamide (1.6 g, 22 mmol) and 10 ml of tetrahydrofuran were mixed, to which 3.06 g (24 mmol) of oxalyl chloride were added dropwise under ice-cooling. After completion of the dropwise addition, the resulting mixture was stirred for further 10 minutes and was then cooled to -15° C. To the mixture so obtained, were added 2.0 g (10 mmol) of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid and 10 ml of tetrahydrofuran, followed by stirring for 80 minutes. The reaction mixture was concentrated under reduced pressure. Slurry was collected by filtration under a nitrogen gas stream and then dried at room temperature, whereby 1.32 g of the title compound were obtained (yield: 43%).

Workup

additionwere added dropwise under ice-
temperaturecooling
additionAfter completion of the dropwise addition
customTo the mixture so obtained
stirringby stirring for 80 minutes
concentrationThe reaction mixture was concentrated under reduced pressure
filtrationSlurry was collected by filtration under a nitrogen gas stream
customdried at room temperature

Sources & evidence

ORD record: ord-43c0ae2acb1b4efd89b9f833e53f78b2
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05650518

Linked notes

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