Di-tert-butyl peroxide → HCID 15169992, compound

HRID 2082420Notes

Reaction equation

[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[N:13]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH:21]=[CH:20]2)[C:12]([CH3:26])([CH3:25])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([O:35][CH:36]1[CH2:41][C:40]([CH3:43])([CH3:42])[N:39]([OH:44])[C:38]([CH3:46])([CH3:45])[CH2:37]1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(OOC(C)(C)C)(C)(C)C>ClC1C=CC=CC=1Cl>[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[N:13]([O:18][CH:19]2[CH2:24][CH2:23][CH:22]([O:44][N:39]3[C:40]([CH3:43])([CH3:42])[CH2:41][CH:36]([O:35][C:27](=[O:34])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:37][C:38]3([CH3:46])[CH3:45])[CH:21]=[CH:20]2)[C:12]([CH3:26])([CH3:25])[CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 135 °C

Procedure

A mixture of 43.6 grams (122 mmol) of the compound prepared in Example 1A, 40.5 grams (147 mmol) of 4-benzoyloxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 17.8 grams (122 mmol) of di-tert-butyl peroxide and 50 ml of 1,2-dichlorobenzene is heated at 135° C. for 5.5 hours in a Fisher-Porter pressure bottle. Fresh di-tert-butyl peroxide (8.0 grams, 55 mmol) is added and the reaction mixture is heated at 135° C. for an additional three hours. The crude reaction mixture is purified by flash chromatography on silica gel (hexane; then 100:3 heptane:ethyl acetate) to afford 4.0 grams of the title compound as a while solid melting at 140°-142° C.

Workup

temperaturethe reaction mixture is heated at 135° C. for an additional three hours
customThe crude reaction mixture
customis purified by flash chromatography on silica gel (hexane

Sources & evidence

ORD record: ord-7a55f71f6ae048e48bc7409a821d3992
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05189086

Reaction notes

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