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

HRID 1377947Notes

Reaction equation

HRID 1377947 reaction equation
[Cl-:1].[CH3:2][N:3]([NH+]=C[Cl:7])[CH3:4].[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:18]/[O:19][CH3:20])/[C:15]([OH:17])=O)[N:13]=1.[CH:21](OC(C)C)(C)C>O1CCCC1>[ClH:7].[CH3:2][N:3]([CH:4]=[N:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:18]/[O:19][CH3:20])/[C:15]([Cl:1])=[O:17])[N:13]=1)[CH3:21]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 5486924(alphaZ)-2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acidHCID 86750850Dimethylaminochloromethyleneammonium chloride

Product 1

HCID 140382097(2Z)-2-[2-(dimethylaminomethylideneamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetyl chloride;hydrochlorideYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-12 °C

Procedure

Dimethylaminochloromethyleneammonium chloride (1.52 g, 12.0 mmol) was dissolved in 7 ml of tetrahydrofuran, followed by cooling to -12° C. Added to the solution were 1.10 g (5.5 mmol) of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid and the resulting mixture was stirred for 40 minutes. Isopropyl ether (16 ml) was added to the reaction mixture, followed by stirring for 40 minutes. Deposited crystals were collected under a nitrogen gas stream, collected by filtration and then dried, whereby 1.65 g of the title compound were obtained (yield: 96.9%).

Workup

  1. additionAdded to the solution
  2. stirringby stirring for 40 minutes
  3. customDeposited crystals were collected under a nitrogen gas stream
  4. filtrationcollected by filtration
  5. customdried

Sources & evidence

ORD record
ord-1819e9726e3949a1be9007bd1b47a227
Source dataset
uspto-grants-1997_09
Patent number
US05665888

Reaction notes

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