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

HRID 1377946Notes

Reaction equation

HRID 1377946 reaction equation
[Cl-].[CH3:2][N:3]([NH+]=C[Cl:7])[CH3:4].Cl.[NH2:9][C:10]1[S:11][CH:12]=[C:13](/[C:15](=[N:19]/[O:20][CH3:21])/[C:16]([Cl:18])=[O:17])[N:14]=1.O1CCC[CH2:23]1>>[ClH:7].[CH3:2][N:3]([CH:4]=[N:9][C:10]1[S:11][CH:12]=[C:13](/[C:15](=[N:19]/[O:20][CH3:21])/[C:16]([Cl:18])=[O:17])[N:14]=1)[CH3:23]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 10131288(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl chloride hydrochlorideHCID 86750850Dimethylaminochloromethyleneammonium chloride

Product 1

HCID 140382097(2Z)-2-[2-(dimethylaminomethylideneamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetyl chloride;hydrochlorideYield 47%

Conditions

Temperature
-10 °C

Procedure

Dimethylaminochloromethyleneammonium chloride (496 mg, 3.87 mmol) was dissolved in 10 ml of tetrahydrofuran, followed by cooling to -10° C. Added to the solution were 870 mg (3.2 mmol) of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetyl chloride hydrochloride and the resulting mixture was stirred for 40 minutes. The reaction mixture was concentrated under reduced pressure. Deposited crystals were collected by filtration under a nitrogen gas stream and then dried at room temperature, whereby 497 mg of the title compound were obtained (yield: 47%).

Workup

  1. additionAdded to the solution
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. filtrationDeposited crystals were collected by filtration under a nitrogen gas stream
  4. customdried at room temperature

Sources & evidence

ORD record
ord-0a7a9cfb35d54233ab25732268152576
Source dataset
uspto-grants-1997_09
Patent number
US05665888

Reaction notes

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