Ethyl Acetate → 2-(4-Phenylsulfanyl-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427600Notes

Reaction equation

CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10]Br.[C:13]1([S:19][C:20]2[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[C:13]1([S:19][C:20]2[CH:27]=[CH:26][C:23]([CH2:24][N:25]3[CH2:10][C:5]4[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=4)[C:3]3=[O:12])=[CH:22][CH:21]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromomethyl-benzoic acid methyl ester (0.230 g, 1 mmol), 4-phenylsulfanyl-benzylamine (0.215 g, 1 mmol), and K2CO3 (0.230 g, 1.67 mmol) in toluene (6 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-(4-phenylsulfanyl-benzyl)-2,3-dihydro-isoindol-1-one (0.175 g, 53%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.27 (s, 2H), 4.77 (s, 2H) 7.22-7.49 (m, 12H), 7.88 (d, 1H). GC-MS: m/z 331 (M)+.

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-b2ae326b7db3424190ad3248984697ba
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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