Diethyl Ether → HCID 14480067, compound

HRID 326418Notes

Reaction equation

HRID 326418 reaction equation
CCOCC.Br[CH2:7][C:8]#[C:9][CH2:10][C:11]#[C:12][CH2:13][C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[CH2:24]([NH:26][C:27](=[O:30])[CH2:28][SH:29])[CH3:25]>C(Cl)Cl>[CH2:24]([NH:26][C:27](=[O:30])[CH2:28][S:29][CH2:7][C:8]#[C:9][CH2:10][C:11]#[C:12][CH2:13][C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:25]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 12736265N-Ethyl-2-sulfanylacetamideHCID 14480083HCID 14480083, compound

Product 1

HCID 14480067HCID 14480067, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The ether solution of 1-bromo-2,5,8-heptadecatriyne, prepared according to the above operating procedure, is added dropwise under an inert atmosphere to a stirred solution, at 0° C., of sodium thiolate of N-ethylthioglycolamide prepared according to operating procedure b) above. The mixture obtained is stirred for 1 hour after the addition is finished. The solvents are then removed by evaporation under vacuum. The product obtained is dissolved in 100 cm3 of methylene chloride. The organic phase is washed with water, dried over magnesium sulphate, concentrated and then deposited onto a silica gel column. The expected amide is eluted with a mixture of methylene chloride and ethyl acetate (97-3). After evaporation of the eluent, 6 g of product are isolated and are recrystallized from isopropyl ether. 4 g of N-ethyl 3-thia-5,8,11-eicosatriynamide are obtained in the form of beige crystals having a melting point of 59° C.

Workup

  1. customprepared
  2. customThe mixture obtained
  3. additionafter the addition
  4. customThe solvents are then removed by evaporation under vacuum
  5. customThe product obtained
  6. washThe organic phase is washed with water
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated
  9. washThe expected amide is eluted with a mixture of methylene chloride and ethyl acetate (97-3)
  10. customAfter evaporation of the eluent, 6 g of product
  11. customare isolated
  12. customare recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-1e8bcf824f054058b353b6dfa5b0b7ed
Source dataset
uspto-grants-1993_12
Patent number
US05268494

Reaction notes

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