Sodium Hydroxide → HCID 135816656, compound

HRID 1493418Notes

Reaction equation

HRID 1493418 reaction equation
Cl[CH2:2][C:3]([O:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:8]([CH3:24])([CH3:23])[CH2:7]1)=[O:4].[CH3:25][C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=1[C:33]1[N:38]=[C:37]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][C:40]=2[CH3:46])[N:36]=[C:35]([C:47]2[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][C:48]=2[OH:54])[N:34]=1.[OH-].[Na+]>CN(C)C=O>[CH3:25][C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=1[C:33]1[N:38]=[C:37]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][C:40]=2[CH3:46])[N:36]=[C:35]([C:47]2[CH:52]=[CH:51][C:50]([O:53][CH2:2][C:3]([O:5][CH:6]3[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:8]([CH3:24])([CH3:23])[CH2:7]3)=[O:4])=[CH:49][C:48]=2[OH:54])[N:34]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 742762-(2,4-Dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazineHCID 19831361HCID 19831361, compound

Product 1

HCID 135816656HCID 135816656, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 14.5 g (40.0 mmol) of 1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl chloroacetate in 25 ml of N,N-dimethylformamide is rapidly added to a mixture of 20.0 g (50.2 mmol) of 2,4-bis(2,4-dimethylphenyl)-6-(2,4-dihydroxyphenyl)-1,3,5-triazine (Example 8A), 125 ml of N,N-dimethylformamide, and 4.0 g of 50% sodium hydroxide solution that has been stirred at ambient temperature for 30 minutes. The reaction mixture is then heated at 70° C. for 1 hour and stirred at ambient temperature for 17 hours. The reaction mixture is partitioned between ethyl acetate (300 ml) and a mixture of water (1000 ml) and 1N hydrochloric acid (10 ml). The aqueous layer is extracted with diethyl (2×500 ml) and saturated sodium chloride solution (500 ml), dried over magnesium sulfate, and concentrated to an oil. Purification by flash chromatography on silica gel (5:1 heptane: ethyl acetate) affords 14.0 g (48% yield) of the title compound, a yellow solid, mp 86°-90° C.

Workup

  1. temperatureThe reaction mixture is then heated at 70° C. for 1 hour
  2. stirringstirred at ambient temperature for 17 hours
  3. customThe reaction mixture is partitioned between ethyl acetate (300 ml)
  4. additiona mixture of water (1000 ml) and 1N hydrochloric acid (10 ml)
  5. extractionThe aqueous layer is extracted with diethyl (2×500 ml) and saturated sodium chloride solution (500 ml)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to an oil
  8. customPurification by flash chromatography on silica gel (5:1 heptane: ethyl acetate)

Sources & evidence

ORD record
ord-4db6dc48ae4d4a7ea4f6feb8c77d53a0
Source dataset
uspto-grants-1991_06
Patent number
US05021478

Reaction notes

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