Thiazole → HCID 70477064, compound

HRID 1583450Notes

Reaction equation

HRID 1583450 reaction equation
[P:1]([O-:26])([O:22][CH2:23][CH2:24]Br)([O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:2].[S:27]1[CH:31]=[CH:30][N:29]=[CH:28]1>>[P:1]([O-:26])([O:22][CH2:23][CH2:24][C:28]1[S:27][CH:31]=[CH:30][NH+:29]=1)([O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:2]

Participants

3

Reactant 2

HCID 9256ThiazoleHCID 20261079HCID 20261079, compound

Product 1

HCID 70477064HCID 70477064, compoundYield 30.8%

Conditions

Temperature
60 °C

Procedure

3,6-Dioxaoctadecyl 2-bromoethyl phosphate (2.5 g) and thiazole (5.0 g) are mixed and heated at 60° C. The excess thiazole is removed under reduced pressure, silver carbonate and methanol are added to the residue, and the mixture is heated under reflux. The insolubles are filtered off, the filtrate is concentrated to dryness, and the residue is purified twice by silica gel column chromatography (developing solvent: methanol; chloroform-methanol-water). There is obtained 0.78 g of the title compound.

Workup

  1. customThe excess thiazole is removed under reduced pressure, silver carbonate and methanol
  2. additionare added to the residue
  3. temperaturethe mixture is heated
  4. temperatureunder reflux
  5. filtrationThe insolubles are filtered off
  6. concentrationthe filtrate is concentrated to dryness
  7. customthe residue is purified twice by silica gel column chromatography (developing solvent: methanol; chloroform-methanol-water)

Sources & evidence

ORD record
ord-27aeb38b63fb4f35b8f66b6c065157e8
Source dataset
uspto-grants-1985_11
Patent number
US04551532

Reaction notes

Loading…