Hydrochloric Acid → HCID 14573453, compound

HRID 2351839Notes

Reaction equation

HRID 2351839 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][C:19]([OH:22])=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl[C:24]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:25].N1C=CC=[CH:37][CH:36]=1.Cl>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][C:19]([O:22][C:24]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:25])=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 81956Carbonochloridic acid, octyl esterHCID 144963952-(4-(Octyloxy)phenyl)pyrimidin-5-ol

Product 1

HCID 14573453HCID 14573453, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

(1.7 g) was hydrogenated in the presence of Pd-C and potassium carbonate in 1,4-dioxane at normal pressure to yield 2-(4-octyloxyphenyl)-5-hydroxypyrimidine (F). (F) (1.0 g) was dissolved in 50 ml of carbon tetrachloride. 0.8 ml of octyl chlorocarboxylate and 5 ml of pyridine were added, and the mixture was stirred for a while and then allowed to stand overnight. 1N hydrochloric acid was added thereto, and the carbon tetrachloride layer was taken and concentrated. The resulting residue was purified by repeated recrystallization from methanol to obtain 2-(4-decyloxyphenyl)-5-octyloxycarbonyloxypyrimidine (A).

Workup

  1. concentrationconcentrated
  2. customThe resulting residue was purified
  3. customrecrystallization from methanol

Sources & evidence

ORD record
ord-18db31d723d44fc0bdd4c3bbe3fe654b
Source dataset
uspto-grants-1989_10
Patent number
US04874542

Reaction notes

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