Sodium Hydroxide → HCID 57013871, compound

HRID 1590957Notes

Reaction equation

HRID 1590957 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([NH:9][CH2:10][CH2:11][CH2:12][CH3:13])[N:3]=1.[CH:14]1([O:20][N:21]2[C:26]([CH3:28])([CH3:27])[CH2:25][CH:24]([NH:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:23][C:22]2([CH3:35])[CH3:34])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[OH-:36].[Na+]>C1(C)C(C)=CC=CC=1>[CH:14]1([O:20][N:21]2[C:22]([CH3:34])([CH3:35])[CH2:23][CH:24]([N:29]([CH2:30][CH2:31][CH2:32][CH3:33])[C:2]3[N:7]=[C:6]([N:29]([CH2:30][CH2:31][CH2:32][CH3:33])[CH:24]4[CH2:23][C:22]([CH3:34])([CH3:35])[N:21]([O:36][CH:19]5[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]5)[C:26]([CH3:28])([CH3:27])[CH2:25]4)[N:5]=[C:4]([NH:9][CH2:10][CH2:11][CH2:12][CH3:13])[N:3]=3)[CH2:25][C:26]2([CH3:27])[CH3:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 12937543N-Butyl-4,6-dichloro-1,3,5-triazin-2-amineHCID 211821294-Butylamino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 57013871HCID 57013871, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 5.0 g (22.5 mmol) of 2,4-dichloro-6-n-butylamino-1,3,5-triazine, 21.1 g (67.8 mmol) of 1-cyclohexyloxy-4-n-butylamino-2,2,6,6-tetramethylpiperidine, 100 ml of xylene, and 5.4 g of 50% aqueous sodium hydroxide is heated at reflux for 16 hours. The reaction mixture is partitioned between ether and water. The ether layer is washed with 1N HCl (2×100 ml), saturated sodium bicarbonate (100 ml) and saturated sodium chloride (100 ml), then dried over magnesium sulfate and concentrated. The crude product is purified by flash chromatography (heptane) and crystallized from ethanol to afford 7.6 g (44% yield) of the title compound, a glass, m.p. 80°-86° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 hours
  3. customThe reaction mixture is partitioned between ether and water
  4. washThe ether layer is washed with 1N HCl (2×100 ml), saturated sodium bicarbonate (100 ml) and saturated sodium chloride (100 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product is purified by flash chromatography (heptane)
  8. customcrystallized from ethanol

Sources & evidence

ORD record
ord-b6a05a111e1544b5a26185e7e80ce693
Source dataset
uspto-grants-1993_04
Patent number
US05204473

Reaction notes

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