Hydrogen Bromide → 2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole

HRID 1632234Notes

Reaction equation

HRID 1632234 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10]O)[N:9]=1)[CH3:3].Cl.[NH2:13][CH2:14][CH2:15][SH:16].Br>C(O)C>[CH3:1][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:16][CH2:15][CH2:14][NH2:13])[N:9]=1)[CH3:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 9082Cysteamine HydrochlorideHCID 1838020(2-((Dimethylamino)methyl)thiazol-4-yl)methanol

Product 1

HCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A reaction mixture was prepared from 18.8 g. of 2-dimethylaminomethyl-4-thiazolemethanol, 12.8 g. of 2-aminoethanethiol hydrochloride (cysteamine hydrocloride) and 160 ml. of 48% aqueous hydrobromic acid. The reaction mixture was stirred at about 100° C. for about 11 hours. The volatile constituents were removed in vacuo on a rotary evaporator. Water was added and the volatile constituents again removed by evaporation. The resulting residue, comprising 2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylamine trihydrobromide formed in the above reaction, was dissolved in ethanol. The ethanol was evaporated and the resulting residue again dissolved in ethanol. Evaporation of the ethanol yielded a hygroscopic residue which was recrystallized from a methanol-ethyl acetate solvent mixture. 2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethylamine trihydrobromide thus prepared had the following physical characteristics:

Workup

  1. customA reaction mixture was prepared from 18.8 g
  2. customThe volatile constituents were removed in vacuo on a rotary evaporator
  3. additionWater was added
  4. customthe volatile constituents again removed by evaporation
  5. customformed in the above reaction
  6. customThe ethanol was evaporated
  7. dissolutionthe resulting residue again dissolved in ethanol
  8. customEvaporation of the ethanol
  9. customyielded a hygroscopic residue which
  10. customwas recrystallized from a methanol-ethyl acetate solvent mixture
  11. custom2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethylamine trihydrobromide thus prepared

Sources & evidence

ORD record
ord-2100487768c647ac93562cda8d8d0e1b
Source dataset
uspto-grants-1984_10
Patent number
US04474794

Reaction notes

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