Diethylamine → Dipropan-2-yl {4-[(N,N-diethylglycyl)oxy]-1,3-dithiolan-2-ylidene}propanedioate

HRID 1763449Notes

Reaction equation

HRID 1763449 reaction equation
[CH3:1][CH:2]([O:4][C:5]([C:7]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[C:8]1[S:12][CH:11]([O:13][C:14]([CH2:16]Cl)=[O:15])[CH2:10][S:9]1)=[O:6])[CH3:3].[CH2:24]([NH:26][CH2:27][CH3:28])[CH3:25]>O1CCCC1>[CH3:25][CH2:24][N:26]([CH2:16][C:14]([O:13][CH:11]1[S:12][C:8](=[C:7]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[C:5]([O:4][CH:2]([CH3:3])[CH3:1])=[O:6])[S:9][CH2:10]1)=[O:15])[CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 3046396Dipropan-2-yl {4-[(chloroacetyl)oxy]-1,3-dithiolan-2-ylidene}propanedioate

Product 1

HCID 3046403Dipropan-2-yl {4-[(N,N-diethylglycyl)oxy]-1,3-dithiolan-2-ylidene}propanedioateYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.8 Grams (0.01 mole) of the diisopropyl ester of 4-chloroacetoxy-1,3-dithiolan-2-ylidene malonic acid obtained in Example 2 was dissolved in 50 ml of tetrahydrofuran. To the resulting solution was added 1.5 g (0.02 mole) of diethylamine, and the resulting mixture was refluxed for 3 hours. After the reaction, the formed diethylamine hydrochloride was removed by filtration, and then the tetrahydrofuran was removed by distillation. The residue was washed with water and then extracted with 1N-HCl. The extract was neutralized with a dilute aqueous sodium hydroxide solution to form an oily substance. This oily substance was extracted with ether, and the ether extract was washed with water, dried and then freed from the ether by distillation, whereby 3.5 g of crude crystals of the desired product were obtained. Subsequently, the crude crystals were recrystallized from n-hexane to obtain 3.1 g of white crystals, m.p. 70.5° - 71° C, yield 74 %.

Workup

  1. temperaturethe resulting mixture was refluxed for 3 hours
  2. customAfter the reaction
  3. customthe formed diethylamine hydrochloride was removed by filtration
  4. customthe tetrahydrofuran was removed by distillation
  5. washThe residue was washed with water
  6. extractionextracted with 1N-HCl
  7. customto form an oily substance
  8. extractionThis oily substance was extracted with ether
  9. extractionthe ether extract
  10. washwas washed with water
  11. customdried
  12. distillationfreed from the ether by distillation, whereby 3.5 g of crude crystals of the desired product
  13. customwere obtained
  14. customSubsequently, the crude crystals were recrystallized from n-hexane

Sources & evidence

ORD record
ord-8da3638856104c79aec7da1fbae6cbb8
Source dataset
uspto-grants-1978_09
Patent number
US04112089

Reaction notes

Loading…