5-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one → 5-(2-Methyl-1,3-thiazol-4-yl)-1,3-dihydro-2H-indol-2-one

HRID 748530Notes

Reaction equation

Cl[CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)=O.[C:15]([NH2:18])(=[S:17])[CH3:16]>C(O)(=O)C>[CH3:16][C:15]1[S:17][CH:2]=[C:3]([C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8]3)[N:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 5-(chloroacetyl)-1,3-dihydro-2H-indol-2-one (1.5 g, 7.15 mmol) and thioacetamide (540 mg, 7.15 mmol) in acetic acid (18 mL) was heated at 80° C. for 3 h. The mixture was cooled to room temperature and the formed precipitate was filtered and washed with ethyl acetate two times and diethyl ether two times and the solid was dried under vacuo to give 1.5 gram (91% yield) of the title compound: 1H NMR (DMSO-d6, 300 MHz) δ 10.49 (s, 1 H), 7.90-7.70 (m, 3 H), 6.85-6.75 (m, 1 H), 3.55 (s, 2 H), 2.70 (s, 3 H).

Workup

temperatureThe mixture was cooled to room temperature
filtrationthe formed precipitate was filtered
washwashed with ethyl acetate two times and diethyl ether two times
customthe solid was dried under vacuo

Sources & evidence

ORD record: ord-6b1fceee4fba4bb68184ccebdba2846d
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399780B2

Reaction notes

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