Sodium Hydroxide → HCID 21243176, compound

HRID 621504Notes

Reaction equation

HRID 621504 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:19]=[C:18]([CH3:20])[N:17]=[C:16]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=4)[CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Br:28][CH2:29][C:30]1([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][C:42]=2[Cl:48])[O:34][CH:33]([CH2:35]OS(C)(=O)=O)[CH2:32][O:31]1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Br:28][CH2:29][C:30]1([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][C:42]=2[Cl:48])[O:34][CH:33]([CH2:35][O:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:13][CH2:12][N:11]([C:14]4[N:19]=[C:18]([CH3:20])[N:17]=[C:16]([C:21]5[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=5)[CH:15]=4)[CH2:10][CH2:9]3)=[CH:6][CH:7]=2)[CH2:32][O:31]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 14074107HCID 14074107, compoundHCID 15576452HCID 15576452, compound

Product 1

HCID 21243176HCID 21243176, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3.605 g (10 mmol) of 1-(4-hydroxyphenyl)-4-(2-methyl-4-(4-tolyl)pyrimidin-6-yl)piperazine, 80 ml of toluene, 4.20 g (10 mmol) of 2-bromomethyl-2-(2,4 -dichlorophenyl)-4-methanesulfonyloxymethyl-1,3-dioxolane (cis/trans mixture), 0.65 g of tetrabutylammonium bromide and 13.5 ml of 50% strength sodium hydroxide solution was stirred vigorously for 4 hours at 55° C. The phases were subsequently separated at room temperature, the sodium hydroxide solution was extracted by shaking three times with ether, and the tolune and ther phases were combined. These were washed three times with water, dried, filtered and evaporated in vacuo. The residue remaining (7.4 g) was chromatographed on a silica gel S/CH2Cl2 column (diameter 2.6 cm, height 11 cm) with elution using CH2Cl2. After elution, the fractions which were unary according to TLC were combined and evaporated in vacuo. 6.27 g (=91.6% yield) of 2-bromomethyl-2 -(2,4-dichlorophenyl)-4-[4-(4-(2-methyl-4-(4-tolyl)pyrimidin-6-yl)piperazin-1-yl)phenoxymethyl]-1,3-dioxolane (cis/trans mixture) were obtained as a highly viscous oil;

Workup

  1. customThe phases were subsequently separated at room temperature
  2. extractionthe sodium hydroxide solution was extracted
  3. stirringby shaking three times with ether
  4. washThese were washed three times with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customwas chromatographed on a silica gel S/CH2Cl2 column (diameter 2.6 cm, height 11 cm) with elution
  9. washAfter elution
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-1dad5e0ea8a444f19f6c3be0c82d5721
Source dataset
uspto-grants-1989_04
Patent number
US04824846

Reaction notes

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