Dinitrofluorobenzene → HCID 20270049, compound

HRID 485293Notes

Reaction equation

HRID 485293 reaction equation
[CH3:1][CH:2]([NH:9][C:10](=[O:25])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]#[C:20][C:21]#[C:22][CH2:23][OH:24])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[N+:33]([C:36]1[CH:41]=[C:40]([N+:42]([O-:44])=[O:43])[CH:39]=[CH:38][C:37]=1F)([O-:35])=[O:34].C(=O)(O)[O-].[K+]>CS(C)=O.O>[CH3:1][CH:2]([NH:9][C:10](=[O:25])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]#[C:20][C:21]#[C:22][CH2:23][O:24][C:37]1[CH:38]=[CH:39][C:40]([N+:42]([O-:44])=[O:43])=[CH:41][C:36]=1[N+:33]([O-:35])=[O:34])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6264DinitrofluorobenzeneHCID 8471TriethylamineHCID 516893Potassium BicarbonateHCID 20270047HCID 20270047, compound

Product 1

HCID 20270049HCID 20270049, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 220 mg (0.65 mmol) of N-(α-methylbenzyl)-14-hydroxy-10,12-tetradecadiynamide in 10 ml DMSO was added 506 mg (5.00 mmol) of triethylamine. To the solution was then added 130 mg (0.70 mmol) of 2,4-dinitrofluorobenzene. The resulting red solution was stirred 16 hours at ambient temperature, and 25 ml of saturated aqueous potassium bicarbonate solution was then added. After stirring 15 minutes, the mixture was poured into 100 ml of water and the resulting solution was extracted with 100 ml portions of ethyl acetate. The combined organic extracts were washed with three 50 ml portions of water and three 50 ml portions of saturated aqueous sodium bicarbonate solution and dried over (MgSO4). Evaporation gave 312 mg of a red oil. NMR indicated no starting alcohol was present. The product was purified by passing it through silica gel (ether as eluent); crystallization from ether petroleum ether gave white crystals, m.p. 59°-60° C. NMR (CDC13): 9.42-7.30, m, 8H aryl H's; 6.00, br s, 1H, N--H; 5.10, br s 2H, O--CH3C=C and m, 1H, CHCH3 ; 2.30, m, 4H, C=CH2CH2 and --CH2CO--; 1.55, d, J=7 Hz, 3H, CH3 and 170--1.20, m, 12 H, other CH2.

Workup

  1. stirringAfter stirring 15 minutes
  2. extractionthe resulting solution was extracted with 100 ml portions of ethyl acetate
  3. washThe combined organic extracts were washed with three 50 ml portions of water and three 50 ml portions of saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over (MgSO4)
  5. customEvaporation

Sources & evidence

ORD record
ord-761674a3d50c48edaa9862937e179e8a
Source dataset
uspto-grants-1985_08
Patent number
US04536450

Reaction notes

Loading…