Water → HCID 178442420, compound

HRID 1731725Notes

Reaction equation

HRID 1731725 reaction equation
[CH2:1]([C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([O:15][C:16]2[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=2)=[O:14])[CH2:9][CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:25]([C:31]1[CH:32]=[N:33][C:34]([OH:37])=[N:35][CH:36]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].O>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH2:1]([C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([O:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([O:37][C:34]3[N:33]=[CH:32][C:31]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:36][N:35]=3)=[O:21])=[CH:18][CH:17]=2)=[O:14])[CH2:9][CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 962WaterHCID 178442421HCID 178442421, compoundHCID 178443908HCID 178443908, compound

Product 1

HCID 178442420HCID 178442420, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of p-(trans-4-hexylcyclohexylcarbonyloxy)-benzoyl chloride (3.9 g) dissolved in toluene was added to a solution of 5-hexylpyrimidin-2-ol (1.0 g) in pyridine (10 ml), followed by stirring at 60° C. for 2 hours, allowing the mixture to stand at room temperature overnight, adding water and toluene to the reaction mixture, separating the toluene layer containing the reaction product, washing the toluene solution twice with 6NHCl (30 ml), washing with water, washing 5 times with 2N NaOH (100 ml), finally washing with water till the washing water became neutral, drying the resulting toluene solution, distilling off low boiling mixture of solvent, etc. under reduced pressure, and recrystallizing crystals obtained from the residue from n-heptanol solvent to obtain the objective compound (2.0 g) (yield 73%), which had a C-N point of 53.3° C. and a N-I point of 125.3° C.

Workup

  1. waitto stand at room temperature overnight
  2. customseparating the toluene layer
  3. additioncontaining the reaction product
  4. washwashing the toluene solution twice with 6NHCl (30 ml)
  5. washwashing with water
  6. washwashing 5 times with 2N NaOH (100 ml)
  7. washfinally washing with water till the washing water
  8. dry with materialdrying the resulting toluene solution
  9. distillationdistilling off low
  10. additionmixture of solvent, etc. under reduced pressure
  11. customrecrystallizing crystals
  12. customobtained from the residue from n-heptanol solvent

Sources & evidence

ORD record
ord-515d0ae836d84e09a0d150a25367f5a4
Source dataset
uspto-grants-1986_11
Patent number
US04623477

Reaction notes

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