3-Methylbenzoyl chloride → 1'-(3-Methylbenzoyl)spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione
Reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([O:11][C:10]3[C:12]4[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=3[S:8][CH2:7]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:3][CH2:2]1.[CH3:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27]>>[CH3:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([N:1]1[CH2:2][CH2:3][C:4]2([O:11][C:10]3[C:12]4[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=3[S:8][CH2:7]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:5][CH2:6]1)=[O:27]Participants
3
Procedure
Compound 60 was synthesized using spiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, 3-methylbenzoyl chloride and conditions outlined in procedure N. M.p.=188-190° C.; 300 MHz 1H NMR (CDCl3) δ 8.08 (d, J=7.8 Hz, 1H), 7.77 (d, J=6.9 Hz, 1H), 7.68 (m, 1H), 7.51 (m, 1H), 7.25 (m, 4H), 4.60 (m, 1H), 3.80 (m, 1H), 3.42 (m 2H), 2.98 (s, 2H), 2.38 (s, 3H), 2.24 (brm, 2H), 1.90 (brm, 2H); LCMS: 420 [M+H].
Sources & evidence
- ORD record
- ord-d0c4c25a23134de5b017716f1a54240e
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039503B2
Reaction notes
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