Hydrochloric Acid → HCID 19979830, compound

HRID 1461196Notes

Reaction equation

HRID 1461196 reaction equation
[C:1]([C:3]([CH3:11])([CH2:7][CH2:8][CH2:9][CH3:10])[C:4]([OH:6])=[O:5])#[N:2].S(Cl)(Cl)=O.[CH2:16]([C:26]1[CH:27]=[N:28][C:29]([C:32]2[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=2)=[N:30][CH:31]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C1N2CCN(CC2)C1.[H-].[Na+].Cl>C1C=CC=CC=1.C(Cl)Cl>[C:1]([C:3]([CH3:11])([CH2:7][CH2:8][CH2:9][CH3:10])[C:4]([O:6][C:35]1[CH:34]=[CH:33][C:32]([C:29]2[N:28]=[CH:27][C:26]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:31][N:30]=2)=[CH:37][CH:36]=1)=[O:5])#[N:2]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 9237DabcoHCID 24386Thionyl Chloride2×HCID 24758Sodium hydrideHCID 14495733HCID 14495733, compound2×HCID 135585902Phenol, 4-(5-decyl-2-pyrimidinyl)-

Product 1

HCID 19979830HCID 19979830, compoundYield 11.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

155 mg (1 mM) of (-)-2-cyano-2-methylhexanoic acid ([α]D -6.15 degrees (c1, methanol)) and 2 ml of thionyl chloride were placed in a dried flask and heat-refluxed in a nitrogen atmosphere, followed by distilling-off of excessive thionyl chloride under reduced pressure. To the resultant acid chloride was added a solution of 312 ml (1 mM) of 4-(5-n-decyl-2-pyrimidyl)phenol and 240 mg (2 mM) of triethylenediamine in 2.5 ml of dry benzene, followed by 2 hours of reaction at 50° C. Further, a solution of 80 mg (2 mM) of sodium hydride in dry benzene was added thereto, followed by 2 hours of reactions. After the reaction, the mixture was cooled to room temperature, followed by addition of 1N-hydrochloric acid and distilled water and extraction with ether. The resultant ether layer was dried on sodium sulfate, followed by distilling-off of the solvent and purification by thin layer chromatography (developer solvent: methylene chloride) to obtain 59 mg of p-(5-n-decyl-2-pyrimidyl)phenyl 2-cyano-2-methylbexanoate. Yield: 11.3% [α]D -3.5 degrees (c1, methylene chloride) m.p.=38°-43° C.

Workup

  1. temperatureheat-refluxed in a nitrogen atmosphere
  2. customfollowed by 2 hours of reaction at 50° C
  3. customAfter the reaction
  4. distillationdistilled
  5. extractionwater and extraction with ether
  6. dry with materialThe resultant ether layer was dried on sodium sulfate
  7. distillationfollowed by distilling-off of the solvent and purification by thin layer chromatography (developer solvent: methylene chloride)
  8. customto obtain 59 mg of p-(5-n-decyl-2-pyrimidyl)phenyl 2-cyano-2-methylbexanoate

Sources & evidence

ORD record
ord-ae6a4d4a701a4cd9aa3362142dba2420
Source dataset
uspto-grants-1991_12
Patent number
US05075031

Reaction notes

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