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

HRID 1758623Notes

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-9b01a9765cd14379bccfde5360abe53e
Source dataset: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04374248

Reaction notes

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