3,5-Dinitrobenzyl alcohol → HCID 58193600, compound

HRID 1922548Notes

Reaction equation

HRID 1922548 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[CH2:7][OH:8])([O-:3])=[O:2].[F:15][C:16]([F:42])([F:41])[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:40]=[CH:39][C:24]([C:25]([O:27][C:28]2[CH:33]=[CH:32][C:31](/[CH:34]=[CH:35]/[C:36](O)=[O:37])=[CH:30][CH:29]=2)=[O:26])=[CH:23][CH:22]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[F:15][C:16]([F:41])([F:42])[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:40]=[CH:39][C:24]([C:25]([O:27][C:28]2[CH:33]=[CH:32][C:31](/[CH:34]=[CH:35]/[C:36]([O:8][CH2:7][C:6]3[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=3)=[O:37])=[CH:30][CH:29]=2)=[O:26])=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 1169783,5-Dinitrobenzyl alcoholHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59850420HCID 59850420, compound

Product 1

HCID 58193600HCID 58193600, compoundYield 7.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.00 g (51.0 mmol) of 3,5-dinitrobenzylalcohol, 2.00 g (51.0 mmol) of (2E)-3-(4-{[4-(4,4,4-trifluorobutoxy)benzoyl]oxy}phenyl)acrylic acid, 62 mg (0.51 mmol) of 4-Dimethylaminopyridine are dissolved in 10 ml of dichloromethane. 1.07 g (56.0 mmol) of N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC hydrochloride) are added at 0° C. The solution is stirred for 1 h at 0° C. and allowed to stir at room temperature overnight. After 22 hours at room temperature the reaction mixture is partitioned between dichloromethane and water. The organic phase is washed repeatedly with water, dried over sodium sulphate, filtered and concentrated by rotary evaporation to yield 3,5-dinitrobenzyl (2E)3-{4-[(4-(4,4,4-trifluorobutoxy)benzoyl)oxy]phenyl}acrylate 2.1 g as colorless crystals.

Workup

  1. stirringto stir at room temperature overnight
  2. customAfter 22 hours at room temperature the reaction mixture is partitioned between dichloromethane and water
  3. washThe organic phase is washed repeatedly with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-142bfb20bbe7447fbce4a5edeca78fee
Source dataset
uspto-grants-2012_05
Patent number
US08173749B2

Reaction notes

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