Allylamine → HCID 178457002, compound

HRID 1758611Notes

Reaction equation

HRID 1758611 reaction equation
CO[C:3]1[C:7](OC)=[N:6][S:5](=[O:11])(=[O:10])[N:4]=1.[CH3:12][N:13]([CH2:15][C:16]1[O:20][C:19]([CH2:21][S:22][CH2:23][CH2:24][NH2:25])=[CH:18][CH:17]=1)[CH3:14].[CH2:26]([NH2:29])[CH:27]=[CH2:28]>CO>[CH2:26]([NH:29][C:7]1[C:3]([NH:25][CH2:24][CH2:23][S:22][CH2:21][C:19]2[O:20][C:16]([CH2:15][N:13]([CH3:12])[CH3:14])=[CH:17][CH:18]=2)=[N:4][S:5](=[O:10])(=[O:11])[N:6]=1)[CH:27]=[CH2:28]

Participants

5

Reactant 3

HCID 7853AllylamineHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 122305383,4-Dimethoxy-1,2,5-thiadiazole 1,1-dioxide

Product 1

HCID 178457002HCID 178457002, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a partial suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide (2.08 g; 11.7 mmoles) in 200 ml of methanol that had been cooled to 0° in an ice-water bath was added dropwise over a period of 45 minutes a solution of 2-[(5-dimethylaminomethyl-2-furyl)methylthio]ethylamine in 30 ml of methanol. When the addition was completed, 10.5 ml of allylamine was added and the solution was allowed to stir at ambient temperature for 18 hours. The reaction mixture was evaporated under reduced pressure and the residue was placed on 120 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 residue crystallized with isopropyl alcohol to give the title compound, mp 83°-86°; the NMR spectrum (100 MHz) in d6 dimethyl sulfoxide showed the presence of approximately 0.9 moles of isopropyl alcohol.

Workup

  1. temperaturehad been cooled to 0° in an ice-water bath
  2. additionWhen the addition
  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 residue crystallized with isopropyl alcohol

Sources & evidence

ORD record
ord-75276ec4dac9486c9d2a32b33f4cd89b
Source dataset
uspto-grants-1983_02
Patent number
US04374248

Reaction notes

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