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

HRID 1665303Notes

Reaction equation

HRID 1665303 reaction equation
[Br:1][C:2]1[CH:20]=[C:19]2[C:5]([C:6](=[O:22])[C:7](=[O:21])[C:8]3[S:18][CH2:17][C:11]4([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]4)[O:10][C:9]=32)=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](Cl)=[O:28]>>[Br:1][C:2]1[CH:20]=[C:19]2[C:5]([C:6](=[O:22])[C:7](=[O:21])[C:8]3[S:18][CH2:17][C:11]4([CH2:16][CH2:15][N:14]([C:27](=[O:28])[C:26]5[CH:30]=[CH:31][CH:32]=[C:24]([Cl:23])[CH:25]=5)[CH2:13][CH2:12]4)[O:10][C:9]=32)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 576618429-Bromospiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Product 1

HCID 576619459-Bromo-1'-(3-chlorobenzoyl)spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Procedure

Compound 68 was synthesized using 9-bromospiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, 3-chlorobenzoyl chloride and conditions outlined in procedure N. M.p.=135-140° C.; 400 MHz 1H NMR (CDCl3) δ: 7.93-7.91 (m, 1H), 7.83-7.82 (m, 1H), 7.67-7.64 (m, 1H), 7.45-7.25 (m, 4H), 4.65-4.5 (bs, 1H), 3.80-3.65 (bs, 1H), 3.55-3.35 (m, 2H), 2.98 (s, 2H), 2.30-2.05 (m, 2H), 2.00-1.67 (m, 2H); LCMS: 518 [M+H].

Sources & evidence

ORD record
ord-65a35872494e47638a73accf744fb55b
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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