Methanol → HCID 86725136, compound

HRID 2204927Notes

Reaction equation

HRID 2204927 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[O:16]1[C:20]2[CH:21]=[CH:22][C:23](/[C:25](=[CH:28]/[C:29]3[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][OH:47])=[C:31]([O:48][CH3:49])[CH:30]=3)/[C:26]#[N:27])=[CH:24][C:19]=2[O:18][CH2:17]1.N1C=CC=CC=1.CO>C1(C)C=CC=CC=1.CN(C=O)C.CN(C)C1C=CN=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7]([O:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][O:35][C:32]1[CH:33]=[CH:34][C:29](/[CH:28]=[C:25](/[C:23]2[CH:22]=[CH:21][C:20]3[O:16][CH2:17][O:18][C:19]=3[CH:24]=2)\[C:26]#[N:27])=[CH:30][C:31]=1[O:48][CH3:49])=[O:8])([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 74323,5-Dinitrobenzoyl chlorideHCID 86725130HCID 86725130, compound

Product 1

HCID 86725136HCID 86725136, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

1.98 g (8.6 mmol) of 3,5-dinitrobenzoyl chloride are dissolved in 16 mL of toluene and 3 drops of DMF were incorporated. 4 g (8.6 mmol) of (2Z)-2-(1,3-benzodioxol-5-yl)-3-{4-[(11-hydroxyundecyl)oxy]-3-methoxyphenyl}prop-2-enenitrile from example 7, 0.052 g (0.4 mmol) of 4-dimethylaminopyridine and 1.03 mL (13 mmol) of pyridine are added. The mixture is stirred at room temperature for 96 hours. The solution is then heated up to 60° C. and 6.5 ml of MeOH are added. The suspension is stirred at room temperature for 1 hour and at 0° C. for 1 hour. The precipitate is filtered off. Recristallisation of the residue in acetonitrile yielded 5.1 g (90%) of pure 11-{4-[(Z)-2-(1,3-benzodioxol-5-yl)-2-cyanoethenyl]-2-methoxyphenoxy}undecyl 3,5-dinitrobenzoate as yellowish powder.

Workup

  1. temperatureThe solution is then heated up to 60° C.
  2. stirringThe suspension is stirred at room temperature for 1 hour and at 0° C. for 1 hour
  3. filtrationThe precipitate is filtered off

Sources & evidence

ORD record
ord-f9ae7d9d73604813b8ce0d9df94b538b
Source dataset
uspto-grants-2016_06
Patent number
US09366906B2

Reaction notes

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