Toluene → HCID 53690215, compound

HRID 982001Notes

Reaction equation

HRID 982001 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][C:6]([CH3:29])=[C:7]([C:23]([O:25][CH2:26][CH2:27][Br:28])=[O:24])[CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:9]=1[C:10]([O:12][CH3:13])=[O:11].[CH2:30]([O:32][CH2:33]Cl)[CH3:31].C1(C)C=CC=CC=1>O1CCCC1.O>[CH2:30]([O:32][CH2:33][N:5]1[C:6]([CH3:29])=[C:7]([C:23]([O:25][CH2:26][CH2:27][Br:28])=[O:24])[CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:4]1[CH3:3])[CH3:31]

Participants

7

Reactant 4

HCID 1140TolueneHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 22158922HCID 22158922, compound

Product 1

HCID 53690215HCID 53690215, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

10.65 g of a 80% suspension of sodium hydride in liquid paraffin are suspended in 300 ml of anhydrous tetrahydrofuran. A solution of 120 g of 3-methyl 5-(2-bromoethyl) (±)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate and 28.4 g of chloromethyl ethyl ether in 300 ml of anhydrous tetrahydrofuran is slowly added dropwise in the course of 4 h at -5° to -7° C., while stirring. After the mixture has been stirred for a further hour at 0° C., 600 ml of toluene and 210 ml of water are added in succession. The phases are separated, and the organic phase is washed with water, dried overnight and evaporated in vacuo. The residue is dissolved in 390 ml of warm ethanol and the stirred solution is then cooled. The product crystallises out during this procedure. It is cooled to 0° C., filtered off under suction, washed with ice-cold ethanol and dried. 98.5 g of the title compound of m.p. 72.5°-74° C. are obtained.

Workup

  1. stirringAfter the mixture has been stirred for a further hour at 0° C.
  2. customThe phases are separated
  3. washthe organic phase is washed with water
  4. customdried overnight
  5. customevaporated in vacuo
  6. dissolutionThe residue is dissolved in 390 ml of warm ethanol
  7. temperaturethe stirred solution is then cooled
  8. customThe product crystallises out during this procedure
  9. filtrationfiltered off under suction
  10. washwashed with ice-cold ethanol
  11. customdried

Sources & evidence

ORD record
ord-5b0fe68cef354ac0b1f567bc5a1c4be7
Source dataset
uspto-grants-1991_02
Patent number
US04994461

Reaction notes

Loading…