Benzylamine → HCID 11501310, compound

HRID 2422044Notes

Reaction equation

Cl[C:2]1[C:3](=[O:18])[N:4]([CH:15]([CH3:17])[CH3:16])[S:5](=[O:14])(=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC#N>[CH2:19]([NH:26][C:2]1[C:3](=[O:18])[N:4]([CH:15]([CH3:17])[CH3:16])[S:5](=[O:14])(=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 120 °C

Procedure

4-Chloro-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.200 g, 0.70 mmol), benzylamine (0.082 g, 0.77 mmol) and TEA (0.078 g, 0.77 mmol) was dissolved in MeCN (3 ml) and heated at in a microwave reactor 120° C. for 5 mins. The reaction mixture was purified by silica gel column chromatography using a 75:25 mixture of heptane and EtOAc as eluant, to give the title compound (0.145 g, 58%). 1H NMR (500 MHz, CDCl3): δ 7.49-7.36 (m, 5H), 7.32-7.26 (m, 3H), 7.05-7.00 (m, 2H), 5.60-5.51 (m, 1H), 4.43 (hep, 1H), 4.08-4.02 (m, 2H), 1.61 (d, 6H); 13C NMR (125 MHz, CDCl3): δ 158.6, 136.5, 135.2, 131.7, 129.8, 129.0, 128.7, 128.1, 127.5, 124.8, 107.9, 48.3, 47.8, 20.3; Mass Spectrum: M−H+ 357.

Workup

customThe reaction mixture was purified by silica gel column chromatography
additiona 75:25 mixture of heptane and EtOAc as eluant

Sources & evidence

ORD record: ord-093b118ef5274f7fb0681c4c005ed5df
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960380B2

Reaction notes

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