Benzoyl chloride, 3-chloro- → 1'-(3-Chlorobenzoyl)-9-methoxyspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

HRID 1665304Notes

Reaction equation

HRID 1665304 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[C:20]2[C:6]([C:7](=[O:23])[C:8](=[O:22])[C:9]3[S:19][CH2:18][C:12]4([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]4)[O:11][C:10]=32)=[CH:5][CH:4]=1.[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:15]1[CH2:16][CH2:17][C:12]2([O:11][C:10]3[C:20]4[C:6]([C:7](=[O:23])[C:8](=[O:22])[C:9]=3[S:19][CH2:18]2)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:21]=4)[CH2:13][CH2:14]1)=[O:29]

Participants

3

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 576618849-Methoxyspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Product 1

HCID 576620021'-(3-Chlorobenzoyl)-9-methoxyspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Procedure

Compound 69 was synthesized using 9-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.=125-127° C.; 400 MHz 1H NMR (CDCl3) δ: LCMS: 7.90 (d, 1H), 7.55-7.47 (m, 3H), 7.41 (m, 1H), 7.25 (d, 1H), 7.11 (dd, 1H), 3.94, (s, 3H), 3.55-3.40 (m, 2H), 3.11 (s, 2H), 2.18-1.92 (m, 4H), 1.89-1.82 (m, 2H); LCMS: 470 [M+H].

Sources & evidence

ORD record
ord-2b9fb46ca575483985f43e9b9279da92
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

Loading…