Chloroform → HCID 19773953, compound

HRID 2372296Notes

Reaction equation

HRID 2372296 reaction equation
C(Cl)(Cl)Cl.C(N(CC)CC)C.[CH2:12]([O:28][C:29]1[CH:30]=[C:31]([C:35]2[N:39]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:38]=[C:37]([OH:46])[CH:36]=2)[CH:32]=[CH:33][CH:34]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[C:47](Cl)(=[O:57])[O:48][CH2:49][CH:50]([CH2:55][CH3:56])[CH2:51][CH2:52][CH2:53][CH3:54]>O>[CH2:55]([CH:50]([CH2:51][CH2:52][CH2:53][CH3:54])[CH2:49][O:48][C:47]([O:46][C:37]1[CH:36]=[C:35]([C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([O:28][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:30]=2)[N:39]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:38]=1)=[O:57])[CH3:56]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 627832-Ethylhexyl chloroformateHCID 178443049HCID 178443049, compound

Product 1

HCID 19773953HCID 19773953, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

50 ml of chloroform and 1.9 ml (0.014 mol) of triethylamine were added to 5.3 g (0.011 mol) of 5-(3-hexadecyloxyphenyl)-3-hydroxy-1-phenylpyrazole to dissolve it, and the solution was stirred at 25° C. 2.3 g (0.012 mol) of 2-ethylhexyl chlorocarbonate was added to the solution dropwise. After stirring for 30 min, cold water was added thereto, and the separated chloroform layer was washed twice with 50 ml of cold water and then dried over Glauber's salt. The Glauber's salt was filtered out, and the chloroform was then removed by distillation. The product thus obtained was purified by column chromatography to produce 5.7 g of exemplified compound I-13 as an oil in a yield of 82%.

Workup

  1. dissolutionto dissolve it
  2. stirringAfter stirring for 30 min
  3. washthe separated chloroform layer was washed twice with 50 ml of cold water
  4. dry with materialdried over Glauber's salt
  5. filtrationThe Glauber's salt was filtered out
  6. customthe chloroform was then removed by distillation
  7. customThe product thus obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-a07a0838fac84af8bcb040c72d164ac8
Source dataset
uspto-grants-1992_03
Patent number
US05098805

Reaction notes

Loading…