2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole → HCID 178494331, compound

HRID 1758620Notes

Reaction equation

HRID 1758620 reaction equation
[CH3:1][O:2][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[S:17][CH:18]=[C:19]([CH2:21][S:22][CH2:23][CH2:24][NH2:25])[N:20]=1)[CH3:14]>CO>[CH3:14][N:13]([CH2:15][C:16]1[S:17][CH:18]=[C:19]([CH2:21][S:22][CH2:23][CH2:24][NH:25][C:7]2[C:3]([O:2][CH3:1])=[N:4][S:5](=[O:11])(=[O:10])[N:6]=2)[N:20]=1)[CH3:12]

Participants

4

Reactant 2

HCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazoleHCID 122305383,4-Dimethoxy-1,2,5-thiadiazole 1,1-dioxide

Product 1

HCID 178494331HCID 178494331, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a cooled (6°) suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide (0.74 g; 4.17 mmoles) in 80 ml of methanol was added dropwise over a period of 45 minutes a solution of 2-[(2-dimethylaminomethyl-4-thiazolyl)methylthio]ethylamine (0.96 g; 4.17 mmoles) [prepared in Step E] to give 3-{2-[(2-dimethylaminomethyl-4-thiazolyl)methylthio]ethylamino}-4-methoxy-1,2,5-thiadiazole 1,1-dioxide, Rf=0.64 [Silica/CH2Cl2 :CH3OH (9:1)]. The temperature was maintained at 6° and anhydrous methylamine was bubbled into the solution for 8 minutes. The reaction mixture was evaporated under reduced pressure and the residue placed on 80 g of silica gel and chromatographed using a gradient elution of methylene chloride-methanol. The appropriate fractions were combined and the residue was rechromatographed on 25 g of aluminum oxide using a gradient elution of methylene chloride-methanol to give 0.52 g of product. Recrystallization from isopropyl alcohol/ether yielded the title compound, mp 144°-148° (foaming).

Workup

  1. temperatureTo a cooled

Sources & evidence

ORD record
ord-592f78e9ad6144c597830274718b316e
Source dataset
uspto-grants-1983_02
Patent number
US04374248

Reaction notes

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