Hydrogen Bromide → HCID 14496389, compound

HRID 1199304Notes

Reaction equation

HRID 1199304 reaction equation
[CH2:1]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=3)=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].Br>C(O)(=O)C>[CH2:1]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][C:19]([C:22]3[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=3)=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 14496388HCID 14496388, compound

Product 1

HCID 14496389HCID 14496389, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 30 g of the above 2-(4-nonylphenyl)-5-(4-methoxyphenyl)pyrimidine, 120 g of 48% hydrobromic acid and 500 ml of acetic acid was refluxed for 40 hours. After acetic acid was distilled away, one liter of water was added to the residue. The obtained crystals were filtered and recrystallized from a solvent of n-heptane-ethyl acetate. 16.3 g of 2-(4-nonylphenyl)-5-(4-hydroxyphenyl)pyrimidine was obtained. This compound showed liquid crystal property and its phase transition temperatures were as follows. ##STR7##

Workup

  1. temperaturewas refluxed for 40 hours
  2. distillationAfter acetic acid was distilled away
  3. additionone liter of water was added to the residue
  4. filtrationThe obtained crystals were filtered
  5. customrecrystallized from a solvent of n-heptane-ethyl acetate

Sources & evidence

ORD record
ord-da2b0e9d27df40f0a69e04629f767774
Source dataset
uspto-grants-1990_02
Patent number
US04900473

Reaction notes

Loading…