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

HRID 736634Notes

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.[CH:12]1([N:18]=[C:19]=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>>[CH:12]1([NH:18][C:19]([N:7]2[C:6](=[O:9])[C:5]3[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][C:4]=3[S:8]2)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

Reactant 2

HCID 6258Ticlatone

HCID 18502Cyclohexyl isocyanate

Product 1

HCID 113013726-Chloro-3-oxo-3H-benzo[d]isothiazole-2-carboxylic acid cyclohexylamide

Procedure

Following the synthetic procedure of 6a as described in Example 1, compound 6y (84% yield) was synthesized from 6-chloro-benzo[d]isothiazol-3-one and cyclohexyl isocyanate as a white solid. IR(CHCl3) 3289, 1711, 1533 cm−1; 1H-NMR (CDCl3) δ1.20-1.48 (m, 5H), 1.58-1.68 (m, 1H), 1.70-1.80 (m, 2H), 1.92-2.05 (m, 2H), 3.80-3.92 (m, 1H), 7.38 (d, J=8.3 Hz, 1H), 7.58 (s, 1H), 7.92 (d, J=8.3 Hz, 1H), 8.75 (d, J=7.8 Hz, 1H); ESIMS m/e 311 and 313 (M++1, 35Cl and 37Cl).

Sources & evidence

ORD record: ord-ba0fea6561e343989242d45d601135c8
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595403B2

Reaction notes

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