Triethylamine → 7-Methyl-9-oxothioxanthene-3-carboxylic acid

HRID 219516

Reaction equation

HRID 219516 reaction equation
Cl.NCCCNC(=O)C(C)=C.[CH3:12][C:13]1[CH:26]=[C:25]2[C:16]([S:17][C:18]3[CH:19]=[C:20]([C:28]([OH:30])=[O:29])[CH:21]=[CH:22][C:23]=3[C:24]2=[O:27])=[CH:15][CH:14]=1.[Cl-].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:12][C:13]1[CH:26]=[C:25]2[C:16]([S:17][C:18]3[CH:19]=[C:20]([C:28]([OH:30])=[O:29])[CH:21]=[CH:22][C:23]=3[C:24]2=[O:27])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103750052-Propenamide, N-(3-aminopropyl)-2-methyl-, hydrochloride (1:1)HCID 86587294HCID 86587294, compound

Product 1

HCID 108259057-Methyl-9-oxothioxanthene-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

N-(3-aminopropyl)methacrylamide hydrochloride (APMA), 4.53 g (25.4 mmol), prepared as described in U.S. Pat. No. 5,858,653, Example 2, was suspended in 100 ml of anhydrous chloroform in a 250 ml round bottom flask equipped with a drying tube. 7-methyl-9-oxothioxanthene-3-carboxylic acid (MTA) was prepared as described in U.S. Pat. No. 4,506,083, Example D. MTA-chloride (MTA-Cl) was made as described in U.S. Pat. No. 6,007,833, Example 1. After cooling the slurry in an ice bath, MTA-Cl, 7.69 g (26.6 mmol), was added as a solid with stirring. A solution of 7.42 ml (53.2 mmol) of triethylamine (TEA) in 20 ml of chloroform was then added over a 1.5 hour time period, followed by a slow warming to room temperature. The mixture was allowed to stir 16 hours at room temperature under a drying tube. After this time, the reaction was washed with 0.1 N HCl and the solvent was removed under vacuum after adding a small amount of phenothiazine as an inhibitor. The resulting product was recrystallized from tetrahydrofuran (THF)/toluene (3/1) and gave 8.87 g (88.7% yield) of product after air drying. The structure of Compound 1 was confirmed by NMR analysis.

Workup

  1. customequipped with a drying tube
  2. temperatureAfter cooling the slurry in an ice bath
  3. additionMTA-Cl, 7.69 g (26.6 mmol), was added as a solid
  4. stirringto stir 16 hours at room temperature under a drying tube
  5. washAfter this time, the reaction was washed with 0.1 N HCl
  6. customthe solvent was removed under vacuum
  7. additionafter adding a small amount of phenothiazine as an inhibitor
  8. customThe resulting product was recrystallized from tetrahydrofuran (THF)/toluene (3/1)

Sources & evidence

ORD record
ord-047053add9cb4430a07515269c0b8420
Source dataset
uspto-grants-2012_06
Patent number
US08202833B2

Linked notes

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