Hydrochloric Acid → HCID 131711177, compound

HRID 2419560Notes

Reaction equation

HRID 2419560 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[S:3][C:2]1=[N:10][CH2:11][CH:12]=[CH:13][N:14]([CH3:16])[CH3:15].[ClH:17]>C(OCC)C>[ClH:17].[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[S:3][C:2]1=[N:10][CH2:11][CH2:12][CH2:13][N:14]([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57046299HCID 57046299, compound

Product 1

HCID 131711177HCID 131711177, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of N'-(1,3-benzodithiol-2-ylidene)-N,N-dimethyl-1,3-propenediamine (3.0g, prepared as described in Example 17) in 100 ml of anhydrous diethyl ether is treated dropwise with ethereal hydrogen chloride until precipitation is completed. The resultant solid is collected by filtration under a nitrogen atmosphere, wwashed several times with anhydrous diethyl ether and recrystallized twice from acetonitrile. The recrystallized product is washed with anhydrous diethyl ether and dried at atmospheric pressure under a slow stream of nitrogen to yield 3.1g of the title compound, melting point 188°-190° C. stirring at room temperature overnight. The reaction mixture is poured into water (2 liters) and extracted three times with 500 ml portions of benzene. The combined benzene layers are dried over anhydrous sodium sulfate and concentrated. The resultant oil is chromatographed on 500 ml of silica gel eluting with benzene (2 liters), chloroform (2 liters) and finally 10% methanol/chloroform (2 liters). The oil obtained from the elution with 10% methanol/chloroform is dissolved in ether, treated with ethereal hydrogen chloride, and filtered under nitrogen. This hygroscopic solid is dissolved in 5% sodium bicarbonate solution and extracted with dichloromethane. The dichloromethane layer is dried over anhydrous sodium sulfate and concentrated. The resultant oil is dissolved in 15 ml of pentane, treated with charcoal, and filtered. The pentane solution was cooled to -78° C in a dry ice acetone bath. After 24 hours, the white precipitate is quickly filtered and transferred to a flask whereup the product is returned to an oil. The oil is dried in vacuo at room temperature overnight to yield 2g of the title compound.

Workup

  1. filtrationThe resultant solid is collected by filtration under a nitrogen atmosphere
  2. customrecrystallized twice from acetonitrile
  3. washThe recrystallized product is washed with anhydrous diethyl ether
  4. customdried at atmospheric pressure under a slow stream of nitrogen

Sources & evidence

ORD record
ord-5b2886d6cadf434aa1f8ed6ec809e926
Source dataset
uspto-grants-1978_08
Patent number
US04107175

Reaction notes

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