Dodecylamine → HCID 178443235, compound

HRID 1758664Notes

Reaction equation

HRID 1758664 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)[CH3:3].CO[C:17]1[C:21](OC)=[N:20][S:19](=[O:25])(=[O:24])[N:18]=1.[CH2:26]([NH2:38])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>CO>[CH3:3][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:17]2[C:21]([NH:38][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[N:20][S:19](=[O:25])(=[O:24])[N:18]=2)=[CH:7][CH:6]=1)[CH3:1]

Participants

5

Reactant 3

HCID 13583DodecylamineHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 122305383,4-Dimethoxy-1,2,5-thiadiazole 1,1-dioxide

Product 1

HCID 178443235HCID 178443235, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of 2-[(5-dimethylaminomethyl-2-furyl)methylthio]ethylamine (2.41 g; 11.2 mmoles) in 25 ml of methanol was added dropwise to a well stirred cold suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide (2.0 g; 11.2 mmoles) in 200 ml of methanol. After stirring at 2°-5° for 15 minutes, a solution of dodecylamine (4.15 g; 22.4 mmoles) in 25 ml of methanol was added all at once, and stirring was continued at ambient temperature for 18 hours. The reaction mixture was filtered and evaporated under reduced pressure, and the residue placed on 60 g of silica gel and chromatographed using a gradient elution of methylene chloride-methanol. The appropriate fractions were combined, evaporated and the residue was rechromatographed on 60 g of silica gel using a gradient elution of acetonitrile-methanol. The appropriate fractions from the second chromatography were combined, concentrated under reduced pressure and the crystallized product was collected by filtration and dried to give 2.13 g of the title compound, mp 136°-139°.

Workup

  1. stirringstirring
  2. waitwas continued at ambient temperature for 18 hours
  3. filtrationThe reaction mixture was filtered
  4. customevaporated under reduced pressure
  5. customchromatographed
  6. washa gradient elution of methylene chloride-methanol
  7. customevaporated
  8. customthe residue was rechromatographed on 60 g of silica gel using
  9. washa gradient elution of acetonitrile-methanol
  10. concentrationconcentrated under reduced pressure
  11. filtrationthe crystallized product was collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-c3f393eb450044f890a217fb543ce3a4
Source dataset
uspto-grants-1983_02
Patent number
US04374248

Reaction notes

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