Propylamine → HCID 178457003, compound

HRID 1758660Notes

Reaction equation

HRID 1758660 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]([NH2:29])[CH2:27][CH3:28]>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:29][CH2:26][CH2:27][CH3:28])=[N:20][S:19](=[O:25])(=[O:24])[N:18]=2)=[CH:7][CH:6]=1)[CH3:1]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 122305383,4-Dimethoxy-1,2,5-thiadiazole 1,1-dioxide

Product 1

HCID 178457003HCID 178457003, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-[(5-dimethylaminomethyl-2-furyl)methylthio]ethylamine (2.41 g; 11.2 mmoles) in 25 ml of dry methanol was added dropwise over a period of 30 minutes to a well stirred suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide (2.0 g; 11.2 mmoles) in 200 ml of dry methanol that had been cooled to 2° in an ice-water bath. After 15 minutes, 4.0 ml of n-propylamine was added all at once and the mixture stirred at ambient temperature for 30 minutes. The reaction mixture was evaporated under reduced pressure and the residue placed on 55 g of silica gel and chromatographed using a gradient elution of methylene chloride-methanol. The appropriate fractions were combined, evaporated under reduced pressure and the syrup crystallized with ether to give 3.7 g of the title compound, mp 164°-166°; the NMR spectrum (100 MHz) in d6 dimethyl sulfoxide showed the presence of approximately 0.9 moles of methanol.

Workup

  1. temperaturehad been cooled to 2° in an ice-water bath
  2. stirringstirred at ambient temperature for 30 minutes
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customchromatographed
  5. washa gradient elution of methylene chloride-methanol
  6. customevaporated under reduced pressure
  7. customthe syrup crystallized with ether

Sources & evidence

ORD record
ord-dac6f7f7dbdf41d4ab263edb50988716
Source dataset
uspto-grants-1983_02
Patent number
US04374248

Reaction notes

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