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

HRID 1702357Notes

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-ba38ef6383ed42a39943acef80f983c8
Source dataset: uspto-grants-1983_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04380639

Reaction notes

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