Methacryloyl chloride → HCID 22725849, compound

HRID 2087076Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]1[C:35](=[O:36])[C:32]2[C:33]3[C:34]4[C:29](=[CH:30][CH:31]=2)[C:28]2[C:37]5[C:24]([C:25]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][OH:44])=[CH:26][CH:27]=2)=[CH:23][CH:22]=[CH:21][C:20]=5[C:19]=4[CH:18]=[CH:17][C:16]=3[C:14]1=[O:15])([CH3:3])[CH3:2].[C:45](Cl)(=[O:49])[C:46]([CH3:48])=[CH2:47]>>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]1[C:35](=[O:36])[C:32]2[C:33]3[C:34]4[C:29](=[CH:30][CH:31]=2)[C:28]2[C:37]5[C:24]([C:25]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][O:44][C:45](=[O:49])[C:46]([CH3:48])=[CH2:47])=[CH:26][CH:27]=2)=[CH:23][CH:22]=[CH:21][C:20]=5[C:19]=4[CH:18]=[CH:17][C:16]=3[C:14]1=[O:15])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 13528Methacryloyl chloride

HCID 22725852HCID 22725852, compound

Product 1

HCID 22725849HCID 22725849, compoundYield 81%

Procedure

Reduction of 2 g (3.2 mmol) of N-(2,6-diisopropylphenyl)-9-(6-acetoxy-1-hexynyl)perylene-3,4-dicarboximide (cf. Example 10, 1.) in accordance with the hydrogenation instructions indicated for alkynylperylenes in Liebigs Ann./Recueil 1997, 395-407 gave a quantitative yield of the corresponding acetoxyhexyl derivative, which could be hydrolyzed as per Example 10, 2. in 98% yield to N-(2,6-diisopropylphenyl)-9-(6-hydroxyhexyl)perylene-3,4-dicarboximide. This, when reacted with methacryloyl chloride in accordance with Example 10, 3., gave the desired product in 81% yield as a red, amorphous solid.

Sources & evidence

ORD record: ord-3882a85e0a5641fd9933ce3cb4939205
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727318B1

Reaction notes

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