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

HRID 736625

Reaction equation

HRID 736625 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:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[CH2:15][N:16]=[C:17]=[O:18]>>[CH3:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[CH2:15][NH:16][C:17]([N:2]1[C:3](=[O:10])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1]1)=[O:18]

Participants

3

Reactant 2

HCID 175201,2-Benzisothiazol-3(2H)-oneHCID 27333873-Methylbenzyl isocyanate

Product 1

HCID 112665083-Oxo-3H-benzo[d]isothiazole-2-carboxylic acid 3-methyl-benzylamide

Procedure

Following the synthetic procedure of 6a as described in Example 1, compound 6k (37% yield) was synthesized from benzo[d]isothiazol-3-one and 3-methylbenzyl isocyanate as a white solid. mp 153-155° C.; IR(CHCl3) 3281, 1711, 1650,1534 cm−1; 1H-NMR (DMSO-d6) δ2.28 (s, 3H), 4.49 (d, J=5.9 Hz, 2H), 7.07 (d, J=7.5 Hz, 1H), 7.12-7.16 (m, 2H), 7.22 (t, J=7.5 Hz, 1H), 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), 9.25 (br t, J=5.9 Hz, 1H); ESIMS m/e 299 (M++1).

Sources & evidence

ORD record
ord-d5f186087b08451897a2d73cbf7b8851
Source dataset
uspto-grants-2009_09
Patent number
US07595403B2

Linked notes

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