1,2-Benzisothiazol-3(2H)-one → 3-Oxo-3H-benzo[d]isothiazole-2-carboxylic acid 4-methyl-benzylamide

HRID 736626

Reaction equation

HRID 736626 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=[O:10])[NH:2]1.[CH3:11][C:12]1[CH:21]=[CH:20][C:15]([CH2:16][N:17]=[C:18]=[O:19])=[CH:14][CH:13]=1>>[CH3:11][C:12]1[CH:21]=[CH:20][C:15]([CH2:16][NH:17][C:18]([N:2]2[C:3](=[O:10])[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:1]2)=[O:19])=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 175201,2-Benzisothiazol-3(2H)-oneHCID 27333881-(Isocyanatomethyl)-4-methylbenzene

Product 1

HCID 112665093-Oxo-3H-benzo[d]isothiazole-2-carboxylic acid 4-methyl-benzylamide

Procedure

Following the synthetic procedure of 6a as described in Example 1, compound 61 (54% yield) was synthesized from benzo[d]isothiazol-3-one and 4-methylbenzyl isocyanate as a white solid. mp 171-173° C.; IR(KBr) 3281, 1711, 1650, 1538 cm−1; 1H-NMR (DMSO-d6) δ2.27 (s, 3H), 4.48 (d, J=5.8 Hz, 2H), 7.14 (d, J=8.2 Hz, 2H), 7.24 (d, J=8.2 Hz, 2H), 7.48 (t, J=7.8 Hz, 1H), 7.78 (t, J=8.2 Hz, 1H), 7.93 (d, J=7.8 Hz, 1H), 8.01 (d, J=8.2 Hz, 1H), 9.22 (br t, J=5.8 Hz, 1H); ESIMS m/e 299 (M++1).

Sources & evidence

ORD record
ord-bff1c90f29a64a3b880c5189771a3953
Source dataset
uspto-grants-2009_09
Patent number
US07595403B2

Linked notes

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