Ticlatone → 6-Chloro-3-oxo-3H-benzo[d]isothiazole-2-carboxylic acid propylamide

HRID 736630Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[NH:7][S:8][C:4]=2[CH:3]=1.[CH2:12]([N:15]=[C:16]=[O:17])[CH2:13][CH3:14]>>[CH2:12]([NH:15][C:16]([N:7]1[C:6](=[O:9])[C:5]2[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][C:4]=2[S:8]1)=[O:17])[CH2:13][CH3:14]

Participants

Reactant 2

HCID 6258Ticlatone

HCID 61033Propyl isocyanate

Product 1

HCID 111499206-Chloro-3-oxo-3H-benzo[d]isothiazole-2-carboxylic acid propylamide

Procedure

Following the synthetic procedure of 6a as described in Example 1, compound 6u (96% yield) was synthesized from 6-chloro-benzo[d]isothiazol-3-one and n-propyl isocyanate as a white solid. IR(KBr) 3294, 1709, 1635, 1520 cm−1; 1H-NMR (CDCl3) δ1.00 (t, J=7.3 Hz, 3H), 1.61-1.71 (m, 2H), 3.38-3.44 (m, 2H), 7.38 (d, J=8.8 Hz, 1H), 7.58 (s, 1H), 7.93 (d, J=8.8 Hz, 1H), 8.79 (br s, 1H); ESIMS m/e 271 and 273 (M++1, 35Cl and 37Cl).

Sources & evidence

ORD record: ord-50f4f6b7c43a439290ad02b749545df9
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595403B2

Reaction notes

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