4-Chlorophenol → 2-tert-Butyl-4-{[3-(4-chlorophenoxy)propyl]amino}-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 2239657Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:7](=[O:23])[N:8]([C:19]([CH3:22])([CH3:21])[CH3:20])[S:9](=[O:18])(=[O:17])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1>>[C:19]([N:8]1[C:7](=[O:23])[C:6]([NH:5][CH2:4][CH2:3][CH2:2][O:31][C:28]2[CH:29]=[CH:30][C:25]([Cl:24])=[CH:26][CH:27]=2)=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[S:9]1(=[O:18])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

Reactant 2

HCID 46844-Chlorophenol

HCID 67242780HCID 67242780, compound

Product 1

HCID 116337482-tert-Butyl-4-{[3-(4-chlorophenoxy)propyl]amino}-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Procedure

The title compound was prepared from 4-[(3-bromopropyl)amino]-2-tert-butyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide and 4-chlorophenol in a similar manner as described for Example 5. 1H NMR (500 MHz CDCl3): δ 7.54-7.48 (m, 2H), 7.46-7.40 (m, 3H), 7.26-7.20 (m, 2H), 6.82-6.76 (m, 2H), 5.72 (t, 1H), 3.86 (t, 2H), 3.11-3.06 (m, 2H), 1.88-1.80 (m, 2H), 1.75 (s, 9H); 13C NMR (125 MHz CDCl3): δ 159.8, 157.1, 135.3, 131.8, 129.8, 129.6, 128.8, 126.2, 125.3, 115.9, 107.3, 66.4, 61.7, 42.4, 28.9, 27.8; Mass Spectrum: M+H+ 449.

Sources & evidence

ORD record: ord-465885a374a44a4db978a0a2e5eb8517
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723333B2

Reaction notes

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