Dimethylamine → 4-Dimethylaminomethyl-2-hydroxymethylthiazole

HRID 2050152Notes

Reaction equation

HRID 2050152 reaction equation
BrC1SC=C(CCl)N=1.CNC.Br[C:13]1[S:14][CH:15]=[C:16]([CH2:18][N:19]([CH3:21])[CH3:20])[N:17]=1.[CH2:22]=[O:23]>C(O)C>[CH3:20][N:19]([CH2:18][C:16]1[N:17]=[C:13]([CH2:22][OH:23])[S:14][CH:15]=1)[CH3:21]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 164271492-Bromo-4-(chloromethyl)thiazoleHCID 204022432-Bromo-4-dimethylaminomethylthiazole

Product 1

HCID 204021554-Dimethylaminomethyl-2-hydroxymethylthiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

When 2-bromo-4-chloromethylthiazole [prepared according to the procedure described in Rev. Roumaine Chim., 10, 897 (1965) (C. A., 64, 8164b 1966)] is reacted with an ethanol solution of dimethylamine and the resultant 2-bromo-4-dimethylaminomethylthiazole is treated with a strong base and formaldehyde according to the general procedure described in Acta Chem. Scand., 20, 2649 (1966) there is produced 4-dimethylaminomethyl-2-hydroxymethylthiazole. When that compound is reacted with thionyl chloride to produce 2-chloromethyl-4-dimethylaminomethylthiazole, and the latter compound is reacted according to the general procedure of Example 15, the title compound is thereby produced.

Sources & evidence

ORD record
ord-4df079b5c8b2479fad6d14f1f723783f
Source dataset
uspto-grants-1980_04
Patent number
US04200578

Reaction notes

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