Cysteamine Hydrochloride → 2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole

HRID 2418049Notes

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].S(Cl)(Cl)=O.C[N:17]([CH2:19][C:20]1[S:21]C=C(CCl)N=1)C.Cl.NCCS>>[CH3:1][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:21][CH2:20][CH2:19][NH2:17])[N:9]=1)[CH3:3]

Participants

Reactant 4

HCID 9082Cysteamine Hydrochloride

HCID 24386Thionyl Chloride

HCID 1838020(2-((Dimethylamino)methyl)thiazol-4-yl)methanol

HCID 1967272N-{[4-(chloromethyl)-1,3-thiazol-2-yl]methyl}-N,N-dimethylamine

Product 1

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

Procedure

When 2-dimethylaminomethyl-4-hydroxymethylthiazole [prepared in Step D] is reacted with thionyl chloride and the resultant 2-dimethylaminomethyl-4-chloromethylthiazole is reacted with an equimolar amount of cysteamine hydrochloride and two equivalents of base according to the general procedure of Example 33, Step D, the title compound is thereby produced.

Sources & evidence

ORD record: ord-7e6b26a1efb0431bb4cb1f222c6fcd40
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04471122

Reaction notes

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