Hydrogen Bromide → 2-{[(1,3,4-Thiadiazol-2-yl)methyl]sulfanyl}ethan-1-amine

HRID 372271Notes

Reaction equation

HRID 372271 reaction equation
CO[CH2:3][C:4]1[S:5][CH:6]=[N:7][N:8]=1.Cl.[NH2:10][CH2:11][CH2:12][SH:13].Br>>[S:5]1[CH:6]=[N:7][N:8]=[C:4]1[CH2:3][S:13][CH2:12][CH2:11][NH2:10]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 9082Cysteamine HydrochlorideHCID 135205782-(Methoxymethyl)-1,3,4-thiadiazole

Product 1

HCID 135205792-{[(1,3,4-Thiadiazol-2-yl)methyl]sulfanyl}ethan-1-amine

Procedure

Equimolar quantities of 2-methoxymethyl(1,3,4)thiadiazole and cysteamine hydrochloride were refluxed under nitrogen for 42 hours in a three-fold excess of hydrobromic acid (48%). The mixture was evaporated to dryness and the residue was dissolved in water. The solution was adjusted to pH 11 by the addition of IRA 400(OH-) and applied to a column of CG50(H+) which was eluted with dilute acetic acid. The eluate was evaporated to give 2-(2-(1,3,4)thiadiazolylmethythio)ethylamine as an oil.

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in water
  3. additionThe solution was adjusted to pH 11 by the addition of IRA 400(OH-)
  4. washwas eluted with dilute acetic acid
  5. customThe eluate was evaporated

Sources & evidence

ORD record
ord-fc1c8159f8764e36993b74f2075040cb
Source dataset
uspto-grants-1978_05
Patent number
US04090026

Reaction notes

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