N-Methylaniline → ethyl 2-(N-methylanilino)-4-thiazolylacetate

HRID 1678876Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[CH3:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH3:13][N:14]([C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 7515N-Methylaniline

HCID 53428667Ethyl 2-(2-bromo-1,3-thiazol-4-yl)acetate

Product 1

HCID 53687162ethyl 2-(N-methylanilino)-4-thiazolylacetateYield 90.5%

Procedure

A mixture of ethyl 2-bromo-4-thiazolylacetate (2.5 g) and N-methylaniline (2.1 g) is stirred at 150°-155° C for 30 minutes. The resultant solution is treated in the same manner as in Example 1 to give ethyl 2-(N-methylanilino)-4-thiazolylacetate (2.5 g).

Sources & evidence

ORD record: ord-c2f37aa23a3c47a2b84d377bc26bade1
Source dataset: uspto-grants-1978_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04077968

Reaction notes

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