5-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one → HCID 17982473, compound

HRID 1387400Notes

Reaction equation

[C:1]([NH2:4])(=[S:3])[CH3:2].[Cl:5][CH2:6][C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12]2)=O>C(O)(=O)C>[ClH:5].[CH3:2][C:1]1[S:3][CH:6]=[C:7]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12]3)[N:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Thioacetamide (90 mg, 1.2 mmol) was added to a slurry of 5-(2-chloro-acetyl)-1,3-dihydro-indol-2-one (250 mg,1.2 mmol) in acetic acid (3 mL). The reaction temperature was increased to 80° C. and stirred at this temperature for 16 h. The reaction mixture was cooled to room temperature and the resultant precipitate was collected by filtration. The solid was washed with EtOAc (2×20 mL) and ether (2×20 mL) and dried in vacuo to afford a cream colored solid (300 mg, 94% yield). 1H NMR (DMSO-d6) δ2.74 (s, 3H); 3.58 (s, 2H); 6.87 (d, 1H); 7.79 (m, 3H); 10.57 (s, 1H). APCI-MS (−ve) m/z 229 (M−H), APCI-MS (+ve) m/z 231 (M+H).Analytical calculated for C12H10N2OS.HCl: C, 54.02; H, 4.16; N, 10.50; S, 12.02. Found: C, 53.73; H, 4.16; N, 10.17; S, 11.63.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationthe resultant precipitate was collected by filtration
washThe solid was washed with EtOAc (2×20 mL) and ether (2×20 mL)
customdried in vacuo

Sources & evidence

ORD record: ord-a6c408e03734424193b36b33f2912c4c
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06268391B1

Reaction notes

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