3-(Trifluoromethyl)benzoyl chloride → 1'-[3-(Trifluoromethyl)benzoyl]spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

HRID 1665289Notes

Reaction equation

HRID 1665289 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.[F:22][C:23]([F:34])([F:33])[C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](Cl)=[O:28]>>[F:22][C:23]([F:33])([F:34])[C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([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:28]

Participants

3

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 57661820Spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Product 1

HCID 576618891'-[3-(Trifluoromethyl)benzoyl]spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Procedure

Compound 54 was synthesized using spiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, 3-(trifluoromethyl)benzoyl chloride and conditions outlined in procedure N. M.p.=165-166° C.; 300 MHz 1H NMR (DMSO-d6) δ 7.70-7.98 (m, 7H), 7.57 (m, 1H), 4.40 (m, 1H), 3.55 (brm, 2H), 3.30 (m, 1H), 3.11 (s, 2H), 2.10 (m, 1H), 1.85 (m, 3H); LCMS: 474 [M+H].

Sources & evidence

ORD record
ord-f5a3f1b71f414c4885f2da2fb2860b0e
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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