1,2-Benzisothiazol-3(2H)-one → 3-Oxo-3H-benzo[d]isothiazole-2-carboxylic acid 2-methyl-benzylamide
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][CH:19]=[CH:18][C:13]=1[CH2:14][N:15]=[C:16]=[O:17]>>[CH3:11][C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[CH2:14][NH:15][C:16]([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:17]Participants
3
Procedure
Following the synthetic procedure of 6a as described in Example 1, compound 6j (56% yield) was synthesized from benzo[d]isothiazol-3-one and 2-methylbenzyl isocyanate as a white solid. mp 184-186° C.; IR(CHCl3) 3281, 1705, 1652, 1528 cm−1; 1H-NMR (DMSO-d6) δ2.32 (s, 3H), 4.52 (d, J=5.9 Hz, 2H), 7.15-7.19 (m, 3H), 7.27-7.30 (m, 1H), 7.48 (t, J=7.6 Hz, 1H), 7.78 (t, J=8.2 Hz, 1H), 7.93 (d, J=8.2 Hz, 1H), 8.01 (d, J=8.2 Hz, 1H), 9.18 (t, J=5.9 Hz, 1H); ESIMS m/e 299 (M++1).
Sources & evidence
- ORD record
- ord-9a25e36f7273476f860b720a3e7cc005
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07595403B2
Reaction notes
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