Dimethylformamide → HCID 88772542, compound

HRID 1278339Notes

Reaction equation

HRID 1278339 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][C:3]=1[SH:9].Cl.[CH3:11][N:12]([CH3:17])[CH2:13][CH2:14][CH2:15]Cl.C(=O)([O-])[O-].[K+].[K+].O.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1.[CH3:36][N:37]([CH3:40])[CH:38]=O>O.CC(O)C>[CH3:35][C:25]1[CH:26]=[CH:27][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:29][CH:30]=1.[CH3:35][C:25]1[CH:26]=[CH:27][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:29][CH:30]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:15][CH2:14][CH2:13][N:12]([CH3:17])[CH3:11])=[CH:4][C:3]=1[S:9][CH2:25][CH2:26][CH2:38][N:37]([CH3:40])[CH3:36]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 941194-Chlorobenzene-1,3-dithiolHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 88772542HCID 88772542, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

A stirred mixture of 8.0 g (0.045 mole) of 4-chloro-m-benzenedithiol, 16.0 g (0.101 mole) of 3-(dimethylamino)propyl chloride hydrochloride and 27.6 g (0.200 mole) of anhydrous potassium carbonate in 250 ml of dimethylformamide was warmed at 70° C. for 2.5 hours, cooled, diluted with water and extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate, filtered and the solvent removed by evaporation. The residue was dissolved in propanol-2, and this solution was treated with a propanol-2 solution of 38.0 g (0.200 mole) of p-toluenesulfonic acid monohydrate. The resulting precipitate was recrystallized from dimethylformamide to give the product, 3,3'-((4-chloro-1,3-phenylene)bis(thio))bis(N,N-dimethyl-1-propanamine) bis(4-methylbenzenesulfonate) as a white, crystalline solid, mp 146.5°-147.5° C.

Workup

  1. temperaturecooled
  2. extractionextracted with methylene chloride
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed by evaporation
  6. dissolutionThe residue was dissolved in propanol-2
  7. customThe resulting precipitate was recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-b01da8120e464e51a7b54a240750d05c
Source dataset
uspto-grants-1981_07
Patent number
US04281118

Reaction notes

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