Tert-Butylamine → HCID 67243051, compound

HRID 2422100Notes

Reaction equation

HRID 2422100 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[C:6]([N:10]1[C:14](=[O:15])[C:13](Cl)=[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:11]1(=[O:24])=[O:23])([CH3:9])([CH3:8])[CH3:7]>>[C:6]([N:10]1[C:14](=[O:15])[C:13]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:11]1(=[O:24])=[O:23])([CH3:9])([CH3:8])[CH3:7]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 672426272-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 67243051HCID 67243051, compoundYield 17%

Procedure

The title compound was prepared as described for Example 24 from tert-butylamine and 2-tert-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide at 140° C. for 1.5 h. The residue was purified by silica gel column chromatography (Horizons Biotage) using 0-5% EtOAc in petroleum ether 40-60° C. as eluent to give the title compound (0.029 g, 17%) as a solid. 1H NMR (500 MHz CDCl3): δ 0.54-7.50 (m, 2H), 7.48-7.44 (m, 3H), 5.53 (s, 1H), 1.74 (s, 9H), 1.08 (s, 9H); 13C NMR (125 MHz CDCl3): 160.9, 133.8, 133.5, 130.3, 129.1, 126.8, 106.6, 61.8, 52.2, 30.1, 27.8; Mass Spectrum: M+H+ 337.

Workup

  1. customThe title compound was prepared
  2. customThe residue was purified by silica gel column chromatography (Horizons Biotage)
  3. custom0-5% EtOAc in petroleum ether 40-60° C.

Sources & evidence

ORD record
ord-9178b0c86d3045c693f2357efbc38878
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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