Pyridine → HCID 178444378, compound

HRID 1680560Notes

Reaction equation

HRID 1680560 reaction equation
C1(S(Cl)(=O)=O)C=CC=CC=1.[CH2:11]([C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]2[CH:23]=[N:24][C:25]([C@H:28]3[CH2:33][CH2:32][C@H:31]([C:34]([NH2:36])=O)[CH2:30][CH2:29]3)=[N:26][CH:27]=2)[CH2:18][CH2:17]1)[CH2:12][CH2:13][CH2:14][CH3:15].N1C=CC=CC=1>C(Cl)Cl>[CH2:11]([C@H:16]1[CH2:17][CH2:18][C@H:19]([C:22]2[CH:27]=[N:26][C:25]([C@H:28]3[CH2:29][CH2:30][C@H:31]([C:34]#[N:36])[CH2:32][CH2:33]3)=[N:24][CH:23]=2)[CH2:20][CH2:21]1)[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 178444379HCID 178444379, compound

Product 1

HCID 178444378HCID 178444378, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

7.2 Ml. of benzenesulfonyl chloride are added dropwise while stirring to a suspension of 13.2 g. of crude trans-4-[5-(trans-4-n-pentylcyclohexyl)-2-pyrimidinyl]cyclohexane carboxamide in 150 ml. of pyridine. The mixture is then warmed to 55° C. for 3 hours in an oil-bath. The mixture is poured into 500 ml. of ice-water and the product is taken up in methylene chloride. The extract is washed successively with 3-N hydrochloric acid, saturated sodium bicarbonate solution and water, dried over sodium sulfate and evaporated. The crude product is chromatographed on a column of 500 g. of silica gel with toluene/5% acetate (v/v). The first fractions are mixtures and are discarded. The later fractions, which are uniform according to thin-layer chromatography, are dissolved in hexane, filtered hot with active carbon and recrystallized from the filtrate. There is obtained pure trans-4-[5-(trans-4-n-pentylcyclohexyl)-2-pyrimidinyl]cyclohexane carbonitrile; melting point 109.5° C., clearing point 175° C.

Workup

  1. additionThe mixture is poured into 500 ml
  2. washThe extract is washed successively with 3-N hydrochloric acid, saturated sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe crude product is chromatographed on a column of 500 g
  6. dissolutionare dissolved in hexane
  7. filtrationfiltered hot with active carbon
  8. customrecrystallized from the filtrate

Sources & evidence

ORD record
ord-7fa9e3cdb8014397911ee9dea861711b
Source dataset
uspto-grants-1981_06
Patent number
US04273929

Reaction notes

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