Triethylamine → HCID 178443718, compound

HRID 1710202Notes

Reaction equation

HRID 1710202 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[S:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)=[N:19][N:20]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N(CC)CC)C.[CH2:35]([C@H:38]1[CH2:43][CH2:42][C@H:41]([CH2:44][CH2:45][C:46](Cl)=[O:47])[CH2:40][CH2:39]1)[CH2:36][CH3:37]>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1.CCOCC>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[S:17][C:18]([C:21]3[CH:22]=[CH:23][C:24]([O:27][C:46](=[O:47])[CH2:45][CH2:44][C@H:41]4[CH2:42][CH2:43][C@H:38]([CH2:35][CH2:36][CH3:37])[CH2:39][CH2:40]4)=[CH:25][CH:26]=3)=[N:19][N:20]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 135734288HCID 135734288, compoundHCID 178447990HCID 178447990, compound

Product 1

HCID 178443718HCID 178443718, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

2-(4-n-Octyloxyphenyl)-5-(4-hydroxyphenyl)-1,3,4-thiadiazole (0.1 mole, 3.82 g) is suspended in 50 mL of absolute toluene and, after addition of 10 mL triethylamine and 100 mg 4-dimethylaminopyridine, treated with stirring with 0.011 moles (2.38 g) 3-(trans-4-n-propylcyclohexyl)-propionyl chloride. The mixture is stirred for 12 hours at room temperature and for 2 hours at 80° C. After being allowed to cool to room temperature, the reaction solution is diluted with 100 mL ether and washed once with 100 mL water, once with 100 mL 5% sodium bicarbonate solution and once again with 100 mL water. After drying over Na2SO4, the solvent is distilled off in a rotary evaporator. The residue is recrystallized from ethanol and methanol until the transition temperature is constant.

Workup

  1. additiontreated
  2. temperatureto cool to room temperature
  3. washwashed once with 100 mL water, once with 100 mL 5% sodium bicarbonate solution and once again with 100 mL water
  4. dry with materialAfter drying over Na2SO4
  5. distillationthe solvent is distilled off in a rotary evaporator
  6. customThe residue is recrystallized from ethanol and methanol until the transition temperature

Sources & evidence

ORD record
ord-57dd87cae94443629ad5544619a1a656
Source dataset
uspto-grants-1990_08
Patent number
US04952699

Reaction notes

Loading…