Propargyl bromide → Ethyl 2-(2-tritylaminothiazol-4-yl)-2-propargyloxyiminoacetate

HRID 2296123Notes

Reaction equation

HRID 2296123 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[C:5]([NH:24][C:25]1[S:26][CH:27]=[C:28]([C:30](=[N:36][OH:37])[C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:29]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:5]([NH:24][C:25]1[S:26][CH:27]=[C:28]([C:30](=[N:36][O:37][CH2:3][C:2]#[CH:1])[C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:29]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 6802348Ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyiminoacetate

Product 1

HCID 54124335Ethyl 2-(2-tritylaminothiazol-4-yl)-2-propargyloxyiminoacetateYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Propargyl bromide (4.16 g.) was added to a suspension of ethyl 2-(2-tritylaminothiazol-4-yl)-2-hydroxyiminoacetate (syn isomer, 10 g.), potassium carbonate (4.84 g.) and N,N-dimethylformamide (22 ml.) under atmosphere of nitrogen gas and stirred at room temperature for 100 minutes. The insoluble substance was filtered off and washed with a little of N,N-dimethylformamide. The filtrate and washing solution were combined together, and water (400 ml.) was added to the solution. After the suspension was extracted with ethyl acetate (400 ml.), the extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After treating the solution with activated charcoal, the solution was concentrated in vacuo. The residue was triturated with diisopropyl ether. The precipitates were collected by filtration, and washed with diisopropyl ether to give ethyl 2-(2-tritylaminothiazol-4-yl)-2-propargyloxyiminoacetate (syn isomer, 8.34 g.).

Workup

  1. filtrationThe insoluble substance was filtered off
  2. washwashed with a little of N,N-dimethylformamide
  3. washThe filtrate and washing solution
  4. additionwater (400 ml.) was added to the solution
  5. extractionAfter the suspension was extracted with ethyl acetate (400 ml.)
  6. washthe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. additionAfter treating the solution with activated charcoal
  9. concentrationthe solution was concentrated in vacuo
  10. customThe residue was triturated with diisopropyl ether
  11. filtrationThe precipitates were collected by filtration
  12. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-01304ff6f7d344be9e3b906dcf8f9b72
Source dataset
uspto-grants-1984_01
Patent number
US04427674

Reaction notes

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