Pyrrolidine → 2-Methyl-5-(pyrrolidinocarbonyl)thiazole

HRID 745717Notes

Reaction equation

[CH3:1][C:2]1[S:3][C:4]([C:7]([O:9]CC)=O)=[CH:5][N:6]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>>[CH3:1][C:2]1[S:3][C:4]([C:7]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:9])=[CH:5][N:6]=1

Participants

Reactant 2

HCID 31268Pyrrolidine

HCID 12808791Ethyl 2-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 233117232-Methyl-5-(pyrrolidinocarbonyl)thiazoleYield 78.6%

Conditions

Temperature: 120 °C

Procedure

A mixture of 15.42 g (0.0901 mole) of ethyl 2-methyl-5-thiazolecarboxylate and 12 g pyrrolidine was stirred at 120° C. under a nitrogen atmosphere for 36 hours to give 12.91 g of the title compound, m.p. 71-2°C. (78.6% yield with respect to the ester).

Sources & evidence

ORD record: ord-6ecdfc27b4b1403395b47dbf0feb3f54
Source dataset: uspto-grants-1986_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04600025

Reaction notes

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