Cinnamyl bromide → 1'-[(2E)-3-phenylprop-2-en-1-yl]spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

HRID 1665337

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.Br[CH2:23]/[CH:24]=[CH:25]/[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[C:26]1(/[CH:25]=[CH:24]/[CH2:23][N:1]2[CH2:2][CH2:3][C:4]3([O:11][C:10]4[C:12]5[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=4[S:8][CH2:7]3)=[CH:16][CH:15]=[CH:14][CH:13]=5)[CH2:5][CH2:6]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Reactant 2

HCID 5357478Cinnamyl bromide

HCID 57661820Spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Product 1

HCID 576620071'-[(2E)-3-phenylprop-2-en-1-yl]spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Procedure

Compound 139 was synthesized using spiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, [(1E)-3-bromoprop-1-en-1-yl]benzene and conditions outlined in procedure V. LCMS: 418 [M+H]; Rt=1.05 min.

Sources & evidence

ORD record: ord-69175ebb9aa841c0a4b2f7dcc7472491
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039503B2

Linked notes

Loading…