Water → HCID 54521452, compound

HRID 894737Notes

Reaction equation

HRID 894737 reaction equation
[CH2:1]([SH:4])[CH:2]=[CH2:3].[CH:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[N:19][O:20][CH2:21][CH2:22]Br)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:12]=1)=[O:6].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([S:4][CH2:22][CH2:21][O:20][N:19]=[C:13]([C:11]1[N:12]=[C:8]([NH:7][CH:5]=[O:6])[S:9][CH:10]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13367Allyl MercaptanHCID 53939076HCID 53939076, compound

Product 1

HCID 54521452HCID 54521452, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Allyl mercaptan (2.12 g.) was added dropwise to a stirred suspension of ethyl 2-(2-formamidothiazol-4-yl)-2-(2-bromoethoxyimino)acetate (syn isomer, 5 g.) and potassium carbonate (3.95 g.) in N,N-dimethylformamide (50 ml.) under ice cooling and stirred at the same temperature for 10 minutes and further at room temperature for 5 hours. After adding water (300 ml.) to the resultant solution, the mixture was extracted with ethyl acetate three times. The extracts were washed twice with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The oily residue was subjected to column chromatography on silica gel and eluted with chloroform. The eluate was concentrated in vacuo to give ethyl 2-(2-allylthioethoxyimino)-2-(2-formamidothiazol-4-yl)acetate (syn isomer, 4.0 g.), mp. 62° to 64° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. washThe extracts were washed twice with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. washeluted with chloroform
  6. concentrationThe eluate was concentrated in vacuo

Sources & evidence

ORD record
ord-b7a902111302461795a5f6997a32ece3
Source dataset
uspto-grants-1981_08
Patent number
US04284631

Reaction notes

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