Trimethylamine → HCID 57898697, compound

HRID 217298Notes

Reaction equation

HRID 217298 reaction equation
C[N:2](C)C.[Cl-].[NH4+].[Cl:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][O:14][CH2:15]2)=[CH:10][C:9]=1[C:18]#[N:19].ClC1C(C#N)=CC=C2C=1CCOC2.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][O:14][CH2:15]2)=[CH:10][C:9]=1[C:18]([NH2:2])=[NH:19]

Participants

7

Reactant 5

HCID 1146TrimethylamineHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 68906541HCID 68906541, compoundHCID 68909027HCID 68909027, compound

Product 1

HCID 57898697HCID 57898697, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of trimethyl amine in toluene (5 ml, 9.8 mmol) was added to a solution of ammonium chloride (0.6 g, 11.1 mmol) in toluene (3 mL) at 0 to 5° C. After the mixture was stirred at room temperature for 1 hour, a mixture (50 mg, 0.26 mmol) of 7-chloroisochromane-6-carbonitrile and 5-chloroisochromane-6-carbonitrile was added thereto. The reaction solution was stirred while heating under reflux overnight. After the reaction solution was cooled to room temperature, an aqueous solution of 2N sodium hydroxide was added and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a 1:0.5 mixture (44 mg, 81%) of the title compound and 5-chloroisochromane-6-carboxamidine.

Workup

  1. stirringThe reaction solution was stirred
  2. temperaturewhile heating
  3. temperatureunder reflux overnight
  4. temperatureAfter the reaction solution was cooled to room temperature
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-767494a2050b4f7fb106270086f165f8
Source dataset
uspto-grants-2012_06
Patent number
US08193351B2

Reaction notes

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