Thiobenzamide → N-[2-[4-(2-Phenyl-thiazol-4-yl)-phenyl]-ethyl}-acetamide

HRID 49382

Reaction equation

[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][C:23](=[O:25])[CH3:24])=[CH:16][CH:15]=1)=O>C(O)C>[C:2]1([C:1]2[S:8][CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][C:23](=[O:25])[CH3:24])=[CH:16][CH:15]=3)[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a round-bottomed flask, thiobenzamide (357 mg, 2.60 mmol) and N-[2-(4-bromoacetyl-phenyl)-ethyl]-acetamide (740 mg, 2.60 mmol) were combined in ethanol (30 ml) and heated to about 80° C. for about three hours. The reaction mixture was then concentrated in vacuo to yield an off-white solid. The resulting material (838 mg, 100% yield) was ascertained to be pure by NMR and was carried into the next step directly without further purification. LRMS ([M+H]+)=323.2.

Workup

concentrationThe reaction mixture was then concentrated in vacuo
customto yield an off-white solid

Sources & evidence

ORD record: ord-8f5947fcc92540b1b934c4e5330ebc07
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706743B2

Linked notes

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