Hydrochloric Acid → HCID 19773971, compound

HRID 2372297Notes

Reaction equation

HRID 2372297 reaction equation
C(N(CC)CC)C.O.[OH:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1.[C:16](Cl)(=[O:25])[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].Cl>C(Cl)(Cl)Cl>[CH2:18]([O:17][C:16]([O:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)=[O:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 118547Carbonochloridic acid, heptyl esterHCID 178526940HCID 178526940, compound

Product 1

HCID 19773971HCID 19773971, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

100 ml of chloroform and 7.3 ml (0.052 mol) of triethylamine were added to 4.5 g (0.040 mol) of 4-hydroxypyridine monohydrate to dissolve it, and the solution was stirred at 25° C. 8.9 g (0.050 mol) of heptyl chlorocarbonate was added to the solution dropwise. After stirring for 30 min, cold aqueous hydrochloric acid was added thereto. After separation the resulting chloroform layer was washed twice with cold water and then dried over Glauber's salt. After filtering out the Glauber's salt, the chloroform was removed by distillation, and the obtained product was purified by column chromatography, followed by crystallization from ethanol, thereby obtaining 7.5 g of exemplified compound I-24 having a melting point of 44° to 50° C. in a yield of 83%.

Workup

  1. dissolutionto dissolve it
  2. stirringAfter stirring for 30 min
  3. customAfter separation the resulting chloroform layer
  4. washwas washed twice with cold water
  5. dry with materialdried over Glauber's salt
  6. filtrationAfter filtering out the Glauber's salt
  7. customthe chloroform was removed by distillation
  8. customthe obtained product was purified by column chromatography
  9. customfollowed by crystallization from ethanol

Sources & evidence

ORD record
ord-655a35be62bf42cab8f93d7b6db8717a
Source dataset
uspto-grants-1992_03
Patent number
US05098805

Reaction notes

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