2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole → HCID 136486310, compound

HRID 1200243Notes

Reaction equation

HRID 1200243 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[CH3:3].CS[C:17](=[N:20][N+:21]([O-:23])=[O:22])[NH:18][CH3:19]>CO>[CH3:19][NH:18][C:17]([NH:14][CH2:13][CH2:12][S:11][CH2:10][C:8]1[N:9]=[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])[S:6][CH:7]=1)=[N:20][N+:21]([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazoleHCID 1362270171,2-Dimethyl-3-nitroisothiourea

Product 1

HCID 136486310HCID 136486310, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction mixture was prepared containing 1.2 g. of 2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylamine, 0.77 g. of S-methyl-N-methyl-N'-nitroisothiourea and 10 ml. of methanol. The reaction mixture was heated under reflux for 4.25 hours, after which time the solvent was removed by evaporation. The partially solid residue was chromatographed over silica using a gradient elution technique employing ethyl acetate containing increasing quantities of methanol as the eluant. Fractions shown by tlc to contain N-methyl-N'-2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl-N"-nitroguanidine formed in the above reaction were pooled and the solvent removed from the pooled fractions. Trituration of the resulting residue with ether yielded a crystalline solid which, upon recrystallization from a methanol-ethyl acetate solvent mixture, yielded 0.83 g. of crystals melting at about 86.5°-88° C.

Workup

  1. customA reaction mixture was prepared
  2. additioncontaining 1.2 g
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for 4.25 hours
  5. customafter which time the solvent was removed by evaporation
  6. customThe partially solid residue was chromatographed over silica using
  7. washa gradient elution technique
  8. temperatureincreasing quantities of methanol as the eluant
  9. customformed in the above reaction
  10. customthe solvent removed from the pooled fractions
  11. customTrituration of the resulting residue with ether yielded a crystalline solid which
  12. customupon recrystallization from a methanol-ethyl acetate solvent mixture
  13. customyielded 0.83 g

Sources & evidence

ORD record
ord-7a8e88ecbf984efaa013067f16f4f198
Source dataset
uspto-grants-1990_02
Patent number
US04904792

Reaction notes

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