Diglycolamine → HCID 86746165, compound

HRID 1886536Notes

Reaction equation

HRID 1886536 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[C:13]([OH:34])(=O)[CH2:14][S:15][CH2:16][C:17]#[C:18][CH2:19][C:20]#[C:21][CH2:22][C:23]#[C:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C(N)COCCO.[Cl-].[NH4+]>ClCCCl>[C:13]([NH2:3])(=[O:34])[CH2:14][S:15][CH2:16][C:17]#[C:18][CH2:19][C:20]#[C:21][CH2:22][C:23]#[C:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 13578DiglycolamineHCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 14480066HCID 14480066, compound

Product 1

HCID 86746165HCID 86746165, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3 g of carbonyldiimidazole are added to a solution of 3.18 g of 3-thia-5,8,11-eicosatriynoic acid in 50 cm3 of 1,2-dichloroethane, stirred at ambient temperature under an inert atmosphere. The mixture thus obtained is heated to a temperature of between 40° and 50° C. for 3 hours. The solution is then cooled to about 10° C. and 2.10 g of diglycolamine are added. 2 hours after the end of the introduction, the reaction mixture is poured into a saturated solution of ammonium chloride. The organic phase is separated off, washed with water, then dried over magnesium sulphate and finally treated with animal charcoal. The solvent is removed by evaporation under vacuum. The product obtained crystallizes on cooling. It is recrystallized from isopropyl ether. 3 g of N --2)-hydroxyethyl) oxyethyl]-3-thia-5,8,11-eicosatriynamide are thus isolated in the form of cream-white crystals having a melting point of 56° C.

Workup

  1. customThe mixture thus obtained
  2. temperatureis heated to a temperature of between 40° and 50° C. for 3 hours
  3. temperatureThe solution is then cooled to about 10° C.
  4. customThe organic phase is separated off
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. additionfinally treated with animal charcoal
  8. customThe solvent is removed by evaporation under vacuum
  9. customThe product obtained
  10. customcrystallizes
  11. temperatureon cooling
  12. customIt is recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-f92a139758104e548c4bafc1fbc7ea62
Source dataset
uspto-grants-1992_09
Patent number
US05151534

Reaction notes

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