Triethylamine → HCID 14418810, compound

HRID 1710204Notes

Reaction equation

HRID 1710204 reaction equation
[CH2:1]([C:10]1[S:11][C:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)=[N:13][N:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].S(Cl)(Cl)=O.[CH2:28]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1O)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH2:1]([C:10]1[S:11][C:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([O:21][C:40]3[CH:41]=[CH:42][C:37]([O:36][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:38][CH:39]=3)=[O:20])=[CH:17][CH:16]=2)=[N:13][N:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 22051939HCID 22051939, compoundHCID 23035827HCID 23035827, compound

Product 1

HCID 14418810HCID 14418810, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

4-(2-n-Nonyl-1,3,4-thiadiazole-5-yl)-benzoic acid (0.005 moles, 1.66 g) is reacted with 5 mL of thionyl chloride and heated 2 hours at the boiling point. After that, the excess thionyl chloride is distilled off in the rotary evaporator and the residue is treated with 0.006 moles (1.33 g) octyloxyphenol, dissolved in 20 mL toluene, 5 mL triethylamine and 100 mg 4-dimethylaminopyridine.

Workup

  1. temperatureheated 2 hours at the boiling point
  2. distillationAfter that, the excess thionyl chloride is distilled off in the rotary evaporator

Sources & evidence

ORD record
ord-e8595434f14a4ddead51b5cf5da76f84
Source dataset
uspto-grants-1990_08
Patent number
US04952699

Reaction notes

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