Allyl bromide → N-allyl-N-[3-(perfluorooctyl)phenyl]-2,4-dinitrobenzenamine

HRID 636337Notes

Reaction equation

[F:1][C:2]([F:44])([C:25]1[CH:26]=[C:27]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][C:33]=2[N+:41]([O-:43])=[O:42])[CH:28]=[CH:29][CH:30]=1)[C:3]([F:24])([F:23])[C:4]([F:22])([F:21])[C:5]([F:20])([F:19])[C:6]([F:18])([F:17])[C:7]([F:16])([F:15])[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10].[CH2:45](Br)[CH:46]=[CH2:47].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[CH2:47]([N:31]([C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([C:2]([F:44])([F:1])[C:3]([F:23])([F:24])[C:4]([F:22])([F:21])[C:5]([F:20])([F:19])[C:6]([F:17])([F:18])[C:7]([F:16])([F:15])[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])[CH:26]=1)[C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][C:33]=1[N+:41]([O-:43])=[O:42])[CH:46]=[CH2:45]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of N-[3-(perfluorooctyl)phenyl]-2,4-dinitrobenzenamine (5.4 g), allyl bromide (1.5 mL), potassium carbonate (2.6 g) and N-methyl pyrrolidone (15 mL) was heated to 60-70° C. for 5.5 hr. Extraction in the normal fashion gave 5.6 g of N-allyl-N-[3-(perfluorooctyl)phenyl]-2,4-dinitrobenzenamine.

Workup

extractionExtraction in the normal fashion

Sources & evidence

ORD record: ord-df1673aeeea54315ba79be3599786af1
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06194039B1

Reaction notes

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