Benzoyl chloride, 3-chloro- → 1'-(3-Chlorobenzoyl)-8-methoxyspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:19](=[CH:20][CH:21]=1)[C:9]1[O:10][C:11]3([CH2:17][S:18][C:8]=1[C:7](=[O:22])[C:6]2=[O:23])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3.[Cl:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=[O:29]>>[Cl:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28]([N:14]1[CH2:15][CH2:16][C:11]2([O:10][C:9]3[C:19]4[C:5]([C:6](=[O:23])[C:7](=[O:22])[C:8]=3[S:18][CH2:17]2)=[CH:4][C:3]([O:2][CH3:1])=[CH:21][CH:20]=4)[CH2:12][CH2:13]1)=[O:29]Participants
3
Procedure
Compound 63 was synthesized using 8-methoxyspiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, 3-chlorobenzoyl chloride and conditions outlined in procedure N. M.p.=130° C. (dec); 400 MHz 1H NMR (DMSO-d6) δ: 7.82 (d, J=8.6 Hz, 1H), 7.55-7.40 (m, 3H), 7.38 (d, J=7.6 Hz, 2H), 7.34 (d, J=7.4 Hz, 1H), 4.42 (bs, 1H), 3.87 (s, 3H), 3.58-3.20 (m, 4H), 3.03 (s, 2H), 2.08-2.02 (m, 2H), 1.96-1.88 (m, 2H), 1.86-1.78 (m, 2H); LCMS: 470 [M+H].
Sources & evidence
- ORD record
- ord-ad10b8eb00ee408c8e8873f09518e391
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039503B2
Reaction notes
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