Cysteamine → HCID 12951539, compound

HRID 614683Notes

Reaction equation

HRID 614683 reaction equation
Br[CH2:2][C:3]1[C:7]([Cl:8])=[N:6][S:5][N:4]=1.[NH2:9][CH2:10][CH2:11][SH:12].[O-]CC.[Na+]>C(O)C>[Cl:8][C:7]1[C:3]([CH2:2][S:12][CH2:11][CH2:10][NH2:9])=[N:4][S:5][N:6]=1

Participants

5

Reactant 3

HCID 6058CysteamineHCID 2723922Sodium ethoxideHCID 21698431HCID 21698431, compound

Product 1

HCID 12951539HCID 12951539, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(4-chloro-3-(1,2,5)-thiadiazolylmethylthio)ethylamine may be prepared by the following route: 3-Methyl(1,2,5)thiadiazole is chlorinated for 4 days in acetonitrile at 25° to give 4-chloro-3-methyl(1,2,5)thiadiazole (oil) which is treated with N-bromosuccinimide in carbon tetrachloride to give 3-bromomethyl-4-chloro(1,2,5)thiadiazole (oil), the 100 MHz n.m.r. in CDCl3 had singlet at 4.66δ. 3-Bromomethyl-4-chloro(1,2,5 )thiadiazole was treated with cysteamine and sodium ethoxide in ethanol to give 2-(4-chloro-3(1,2,5)thiadiazolylmethylthio)ethylamine (oil). A 60 MHz n.m.r. spectrum (CDCl3) gave a singlet at 3.91 attributed to the Het-CH2 -S protons.

Sources & evidence

ORD record
ord-b135c162857c4675830e4283a02ce6f0
Source dataset
uspto-grants-1979_03
Patent number
US04145546

Reaction notes

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