Triethylamine → HCID 19766008, compound

HRID 1591033Notes

Reaction equation

HRID 1591033 reaction equation
C(N(CC)CC)C.[C:8]([C:10]1[S:14][N:13]=[C:12]([CH3:15])[C:11]=1[N+:16]([O-:18])=[O:17])#[N:9].[CH2:19]([S:31]([C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1)(=[O:33])=[O:32])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].[OH-].[Na+]>O1CCCC1>[C:8]([C:10]1[S:14][N:13]=[C:12]([CH2:15][C:38](=[O:39])[C:37]2[CH:36]=[CH:35][C:34]([S:31]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])(=[O:33])=[O:32])=[CH:42][CH:41]=2)[C:11]=1[N+:16]([O-:18])=[O:17])#[N:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 21785282HCID 21785282, compoundHCID 23437554HCID 23437554, compound

Product 1

HCID 19766008HCID 19766008, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (20.2 grams, 0.200 mol) was added to 200 ml of a tetrahydrofuran (THF) solution of 16.9 grams (0.100 mol) of 5-cyano-3-methyl-4-nitroisothiazole, and 74.6 grams (0.200 mol) of 4-dodecylsulfonylbenzoyl chloride was added dropwise. After heating under reflux for 8 hours, 200 ml of 1N aqueous sodium hydroxide solution was added dropwise. After heating under reflux for 3 hours, the reaction mixture was left to cool, poured into ice water and extracted with ethyl acetate. 5-Cyano-3-(4-dodecylsulfonylbenzoylmethyl)-4-nitroisothiazole (11.9 grams, 23.5 mmol) was obtained on refinement using silica gel column chromatography.

Workup

  1. additionwas added dropwise
  2. temperatureAfter heating
  3. temperatureunder reflux for 8 hours
  4. temperatureAfter heating
  5. temperatureunder reflux for 3 hours
  6. waitthe reaction mixture was left
  7. temperatureto cool
  8. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-287ccc0403064a6b9be340e2c1750860
Source dataset
uspto-grants-1993_04
Patent number
US05206129

Reaction notes

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