Cysteamine Hydrochloride → 1-Nitro-2-methylthio-2-{2-[(4-methylthiazol-2-yl)methylthio]ethylamino}ethylene

HRID 2050150Notes

Reaction equation

HRID 2050150 reaction equation
Cl[CH2:2][C:3]1[S:4][CH:5]=[C:6]([CH3:8])[N:7]=1.S(Cl)(Cl)=O.OCC1SC=C(C)N=1.Cl.[NH2:22][CH2:23][CH2:24][SH:25].C[O-].[Na+].[CH3:29][S:30][C:31](SC)=[CH:32][N+:33]([O-:35])=[O:34]>>[N+:33]([CH:32]=[C:31]([S:30][CH3:29])[NH:22][CH2:23][CH2:24][S:25][CH2:2][C:3]1[S:4][CH:5]=[C:6]([CH3:8])[N:7]=1)([O-:35])=[O:34]

Participants

7

Reactant 6

HCID 9082Cysteamine HydrochlorideHCID 24386Thionyl ChlorideHCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 10942334Sodium MethoxideHCID 112750912-(Chloromethyl)-4-methyl-1,3-thiazoleHCID 17750909(4-Methyl-1,3-thiazol-2-yl)methanol

Product 1

HCID 705962611-Nitro-2-methylthio-2-{2-[(4-methylthiazol-2-yl)methylthio]ethylamino}ethylene

Procedure

When 2-chloromethyl-4-methylthiazole [prepared by the reaction of thionyl chloride and 2-hydroxymethyl-4-methylthiazole, which itself is prepared according to the procedure of J. Chem. Soc., (Suppl. Issue No. 1), S106-111 (1966) or Acta Chem. Scand., 20, 2649 (1966)] is reacted with cysteamine hydrochloride and about two equivalents of a strong base such as sodium methoxide, and the resultant amine is treated with 1,1-bis(methylthio)-2-nitroethylene, there is produced 1-nitro-2-methylthio-2-{2-[(4-methylthiazol-2-yl)methylthio]ethylamino}ethylene. When the latter compound is reacted with propargylamine according to the general procedure of Example 1, there is produced 1-nitro-2-(2-propynylamino)-2-{2-[(4-methylthiazol-2-yl)methylthio]ethylamino}ethylene.

Workup

  1. customis prepared

Sources & evidence

ORD record
ord-482b3f007e6f4d7ca39b63883eb2e203
Source dataset
uspto-grants-1980_04
Patent number
US04200578

Reaction notes

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