Potassium Carbonate → HCID 88475937, compound

HRID 1649755Notes

Reaction equation

HRID 1649755 reaction equation
Cl.[C:2]([NH:21][C:22]1[S:23][CH:24]=[C:25](/[C:27](=[N:33]/[OH:34])/[C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:26]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH3:48]>CN(C)C=O>[C:2]([NH:21][C:22]1[S:23][CH:24]=[C:25](/[C:27](=[N:33]/[O:34][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH3:48])/[C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:26]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1235321-Bromo-3,6-dioxaheptaneHCID 9589415(Z)-Ethyl 2-(hydroxyimino)-2-(2-(tritylamino)thiazol-4-yl)acetate hydrochloride

Product 1

HCID 88475937HCID 88475937, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 50 ml of dimethylformamide is dissolved 7.41 g of ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-hydroxyiminoacetate hydrochloride and with stirring at room temperature, 4.15 g of potassium carbonate and 2.75 g of 1-bromo-2-(2-methoxyethoxy)ethane are added. The mixture is stirred for 48 hours, after which it is poured into 500 ml of ice water and extracted with ethyl acetate. The extract is washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica gel (150 g) column and elution is carried out with hexane-ethyl acetate (1:1). The fractions rich in the desired compound are pooled and concentrated under reduced pressure to give 4.84 g of ethyl 2-(2-tritylaminothiazol4-yl)-(Z)-2-[2-(2-methoxyethoxy)ethoxyimino]acetate as a yellow foamy product.

Workup

  1. stirringThe mixture is stirred for 48 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is chromatographed on silica gel (150 g) column and elution
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e272566b3de1459c89de0ac58967c9d5
Source dataset
uspto-grants-1990_05
Patent number
US04921851

Reaction notes

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