2-Phenoxyethanamine → 2-tert-Butyl-4-[(2-phenoxyethyl)amino]-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 2422048Notes

Reaction equation

HRID 2422048 reaction equation
[O:1]([CH2:8][CH2:9][NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([N:15]1[C:19](=[O:20])[C:18](Cl)=[C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[S:16]1(=[O:29])=[O:28])([CH3:14])([CH3:13])[CH3:12]>>[C:11]([N:15]1[C:19](=[O:20])[C:18]([NH:10][CH2:9][CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[S:16]1(=[O:28])=[O:29])([CH3:14])([CH3:12])[CH3:13]

Participants

3

Reactant 2

HCID 156512-PhenoxyethanamineHCID 672426272-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 115314332-tert-Butyl-4-[(2-phenoxyethyl)amino]-5-phenylisothiazol-3(2H)-one 1,1-dioxideYield 13%

Procedure

The title compound was prepared as described for Example 24 from (2-phenoxyethyl)amine and 2-tert-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide. The residue was purified by silica gel column chromatography (Horizons Biotage) using 15-20% EtOAc in petroleum ether 40-60° C. as eluent to give the title compound (0.026 g, 13%). 1H NMR (500 MHz CDCl3): δ 7.60-7.51 (m, 2H), 4.72-7.42 (m, 2H), 7.29 (t, 2H), 6.99 (t, 1H), 6.84 (d, 2H), 5.67 (t, 1H), 3.89 (t, 2H), 3.25 (q, 2H), 1.75 (s, 9H); 13C NMR (125 MHz CDCl3): δ 159.7, 158.3, 135.2, 131.7, 129.5, 129.8, 129.0, 125.2, 121.7, 114.7, 108.1, 65.9, 61.8, 43.5, 27.8; Mass Spectrum M+H+ 401.

Workup

  1. customThe title compound was prepared
  2. customThe residue was purified by silica gel column chromatography (Horizons Biotage)
  3. custom15-20% EtOAc in petroleum ether 40-60° C.

Sources & evidence

ORD record
ord-61b1ffe794ab43b8a0948513fb93f46e
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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