Methanethiol → 2-Amidino-4-hydroxy-1,2,3,4-tetrahydroisoquinoline sulfate

HRID 436780Notes

Reaction equation

HRID 436780 reaction equation
[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].CS[C:8](=[NH:10])[NH2:9].[OH:11][CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][NH:14][CH2:13]1.CS>O>[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[C:8]([N:14]1[CH2:13][CH:12]([OH:11])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15]1)(=[NH:9])[NH2:10]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 752702-Methyl-2-thiopseudourea sulfateHCID 117447921,2,3,4-Tetrahydroisoquinolin-4-ol

Product 1

HCID 125230402-Amidino-4-hydroxy-1,2,3,4-tetrahydroisoquinoline sulfate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.3 g. of S-methyl-isothiourea sulfate in 5 ml. of water at about 20° C. was added to 1.2 g. of 4-hydroxy-1,2,3,4-tetrahydroisoquinoline. The resulting mixture was maintained at about 25°-30° C. with occasional shaking. After a short time, methyl-mercaptan began to escape and, upon standing for 1-2 days, crystals formed. The crystals were removed by filtration and rinsed with ice-cold water and with ether. Recrystallization from water yielded 2-amidino-4-hydroxy-1,2,3,4-tetrahydroisoquinoline sulfate, having a melting point of 264°-266° C. (uncorrected).

Workup

  1. temperatureThe resulting mixture was maintained at about 25°-30° C. with occasional shaking
  2. customcrystals formed
  3. customThe crystals were removed by filtration
  4. washrinsed with ice-cold water and with ether
  5. customRecrystallization from water

Sources & evidence

ORD record
ord-5ce8d4ca6c68469f9ddd8a5f1810134e
Source dataset
uspto-grants-1977_06
Patent number
US04028363

Reaction notes

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