Hydrochloric Acid → HCID 54011248, compound

HRID 1461195Notes

Reaction equation

HRID 1461195 reaction equation
C(O[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]=1[C:24]([OH:26])=[O:25])CCCCCCCCC.S(Cl)(Cl)=O.O[C:32]1[CH:49]=[CH:48][C:35]([C:36]([O:38][CH2:39][C:40]([C:46]#[N:47])([CH3:45])[CH2:41][CH2:42][CH2:43][CH3:44])=[O:37])=[CH:34][CH:33]=1.[H-].[Na+].Cl>C1C=CC=CC=1.CCOCC.O>[CH2:24]([O:25][C:17]1[CH:12]=[C:13]([C:24]([O:26][C:32]2[CH:49]=[CH:48][C:35]([C:36]([O:38][CH2:39][C:40]([C:46]#[N:47])([CH3:45])[CH2:41][CH2:42][CH2:43][CH3:44])=[O:37])=[CH:34][CH:33]=2)=[O:25])[C:14]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:15][CH:16]=1)[CH2:13][CH2:12][CH2:17][CH2:16][CH2:15][CH2:14][CH2:18][CH2:19][CH3:20]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 24386Thionyl Chloride2×HCID 24758Sodium hydrideHCID 14793450HCID 14793450, compoundHCID 19898360HCID 19898360, compound

Product 1

HCID 54011248HCID 54011248, compoundYield 129.3%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

211 mg (1.18 mM) of decyloxybiphenylcarboxylic acid and 2.5 ml of thionyl chloride were heat-refluxed for 2 hours, followed by distilling-off of excessive thionyl chloride. To the resultant acid chloride was added a solution of 339 mg (1.18 mM) of 2-cyano-2-methylhexyl p-hydroxybenzoate and 263 mg (2.36 mM) of thiethylenediamine in 5 ml of dry benzene, followed by 2 hours of stirring under heating at 50° C. Then, a solution of 56.5 mg (2.36 mM) of sodium hydride in 2 ml of dry benzene was added, followed by 2 hours of heat-refluxing. After the reaction, the mixture was cooled to room temperature, followed by addition of 5 ml of 1N-hydrochloric acid and 12 ml of distilled water and extraction with ether. The ether solution was dried on sodium sulfate, followed by distilling-off of the solvent and purification by thin layer chromatography (developer solvent: benzene/methylene chloride=1:3) to obtain 230 mg of 2-cyano-2 -methylhexyl p-(p-decyloxybiphenyl carbonyloxy)benzoate. Yield: 32.1%. [α]D -4.6 degrees (c1, methylene chloride). Phase transition temperatures (°C.): ##STR34##

Workup

  1. waitfollowed by 2 hours
  2. temperatureof heat-refluxing
  3. customAfter the reaction
  4. temperaturethe mixture was cooled to room temperature
  5. dry with materialThe ether solution was dried on sodium sulfate
  6. distillationfollowed by distilling-off of the solvent and purification by thin layer chromatography (developer solvent: benzene/methylene chloride=1:3)

Sources & evidence

ORD record
ord-e9eda5d15c45446c84f6057fbb52ad53
Source dataset
uspto-grants-1991_12
Patent number
US05075031

Reaction notes

Loading…