Hydrochloric Acid → HCID 19773971, compound

HRID 1613536Notes

Reaction equation

HRID 1613536 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, compound

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 and dissolved in 4.5 g (0.040 mol) of 4-hydroxypyridine-monohydrate and stirred at 25° C. To this was dropwise added 8.9 g (0.050 mol) of heptyl chlorocarbonate. After stirring for 30 minutes, a cold aqueous hydrochloric acid solution was added to the reaction mixture for liquid separation, and the chloroform layer separated was washed two times with cold water and dried with Glauber's salt. After the Glauber's salt was filtrated out, the chloroform was distilled out and the remaining precipitate was purified by column chromatography and crystallized in ethanol. The product had a melting point of from 44° to 50° C. Yield: 7.5 g, 83%.

Workup

  1. stirringAfter stirring for 30 minutes
  2. customthe chloroform layer separated
  3. washwas washed two times with cold water
  4. dry with materialdried with Glauber's salt
  5. filtrationAfter the Glauber's salt was filtrated out
  6. distillationthe chloroform was distilled out
  7. customthe remaining precipitate was purified by column chromatography
  8. customcrystallized in ethanol
  9. customof from 44° to 50° C

Sources & evidence

ORD record
ord-09744e6262d54486b64ed19ef7072a1b
Source dataset
uspto-grants-1993_03
Patent number
US05194348

Reaction notes

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