Methylamine → HCID 178482516, compound

HRID 1980720Notes

Reaction equation

HRID 1980720 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:6][C:7]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[CH:8][N:9]=1)[CH3:3].CO[C:17]1[C:21](OC)=[N:20][S:19](=[O:25])(=[O:24])[N:18]=1.[CH3:26][NH2:27]>CO>[CH3:3][N:2]([CH2:4][C:5]1[S:6][C:7]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:17]2[C:21]([NH:27][CH3:26])=[N:20][S:19](=[O:25])(=[O:24])[N:18]=2)=[CH:8][N:9]=1)[CH3:1]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 122305383,4-Dimethoxy-1,2,5-thiadiazole 1,1-dioxideHCID 15592304HCID 15592304, compound

Product 1

HCID 178482516HCID 178482516, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-[(2-dimethylaminomethylthiazol-5-yl)methylthio]ethylamine (1.55 g; 6.7 mmoles) [prepared in Step D] in 60 ml of methanol was added dropwise over 40 minutes to a partial suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide (1.19 g; 6.7 mmoles) in 130 ml of methanol that had been cooled to 8°. Upon completion of the addition, anhydrous methylamine was bubbled into the solution for 8 minutes, then stirred at ambient temperature overnight. The reaction mixture was evaporated under reduced pressure and the residue chromatographed on 150 g of silica gel using a gradient elution of acetonitrile-methanol. The appropriate fractions were combined to give 1.05 g of product. Recrystallization from 2-propanol yielded the title compound, mp 170°-172°.

Workup

  1. temperaturehad been cooled to 8°
  2. customwas bubbled into the solution for 8 minutes
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customthe residue chromatographed on 150 g of silica gel using
  5. washa gradient elution of acetonitrile-methanol

Sources & evidence

ORD record
ord-510be955e947404eb0ba2cfcf712b359
Source dataset
uspto-grants-1985_04
Patent number
US04510309

Reaction notes

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