2,3-Diaza-spiro[4.4]non-2-ene → 4-(tert-Butyl-diphenyl-silanyloxymethyl)-N-[(2,3-diaza-spiro[4.4]non-3-en-2-yl)-methylsulfanyl-methylene]-benzenesulfonamide

HRID 1044686Notes

Reaction equation

[CH3:1][S:2][C:3](SC)=[N:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:15][SiH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[CH2:35]1[C:39]2([CH2:43][CH2:42][CH2:41][CH2:40]2)[CH2:38][N:37]=[N:36]1>N1C=CC=CC=1>[C:17]([SiH2:16][O:15][C:14]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:11]1[CH:10]=[CH:9][C:8]([S:5]([N:4]=[C:3]([N:36]2[N:37]=[CH:38][C:39]3([CH2:43][CH2:42][CH2:41][CH2:40]3)[CH2:35]2)[S:2][CH3:1])(=[O:7])=[O:6])=[CH:13][CH:12]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 90 °C

Procedure

To 15 mL pyridine, 400 mg N-(bis-methylsulfanyl-methylene)-4-(tert-butyl-diphenyl-silanyloxymethyl)-benzenesulfonamide and 111 mg 2,3-diaza-spiro[4.4]non-2-ene were added. The mixture was heated for two nights at 90° C. degrees, concentrated under reduced pressure and dried in vacuo to provide 700 mg of product (LC-MS Rt 3.91 min) which was used in the subsequent step without purification. 1H NMR (400 MHz, CDCl3) δ ppm 1.10-1.12 (m, 9H), 1.63-1.94 (m, 8H), 4.82 (s, 2H), 7.01 (s, 1H), 7.65-7.71 (m, 4H), 7.92-7.96 (m, 2H).

Workup

concentrationconcentrated under reduced pressure
customdried in vacuo

Sources & evidence

ORD record: ord-950f0bdc9981488bb02a19e5c44ae377
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563723B2

Reaction notes

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