Potassium Carbonate → 1-[4-(4-(Dimethylamino)naphthylazo)-phenylazo]-4-(6-acryloyloxyhexyloxy)naphtalene

HRID 28317Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture consisting of 0.44 g of 1-[4-(4-(dimethylamino)naphthylazo)phenylazo]-4-hydroxy-naphtalene, 0.56 g of 6-iodohexyl acrylate, and 0.28 g of potassium carbonate in 10 ml of DMF was stirred under nitrogen atmosphere for 3 h at 60° C. After cooling to room temperature the reaction mixture was quenched with 100 ml 3N HCl and the resulting precipitate was filtered off, washed with water (100 ml) and ethanol (50 ml) to give 0.5 g of pure 1-[4-(4-(dimethylamino)naphthylazo)-phenylazo]-4-(6-acryloyloxyhexyloxy)naphtalene as a brownish powder; λmax. (CB 483): 504 nm.

Workup

temperatureAfter cooling to room temperature the reaction mixture
customwas quenched with 100 ml 3N HCl
filtrationthe resulting precipitate was filtered off
washwashed with water (100 ml) and ethanol (50 ml)

Sources & evidence

ORD record: ord-92f36e32dd5d4bacbd6092f3ab38af0a
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419620B2

Reaction notes

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