Pyridine → HCID 178442518, compound

HRID 1680558Notes

Reaction equation

HRID 1680558 reaction equation
C1(S(Cl)(=O)=O)C=CC=CC=1.[CH2:11]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:25]=[N:26][C:27]([C@H:30]3[CH2:35][CH2:34][C@H:33]([C:36]([NH2:38])=O)[CH2:32][CH2:31]3)=[N:28][CH:29]=2)=[CH:20][CH:19]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].N1C=CC=CC=1>C(Cl)Cl>[CH2:11]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[N:28][C:27]([C@H:30]3[CH2:31][CH2:32][C@H:33]([C:36]#[N:38])[CH2:34][CH2:35]3)=[N:26][CH:25]=2)=[CH:20][CH:19]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 178442519HCID 178442519, compound

Product 1

HCID 178442518HCID 178442518, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

6.0 Ml. of benzenesulfonyl chloride are added dropwise while stirring to a suspension of 10.8 g. of trans-4-[5-(p-n-heptylphenyl)-2-pyrimidinyl]cyclohexane carboxamide in 150 ml. of pyridine. The mixture is then warmed to 55° C. for 2 hours in an oilbath. The mixture is poured into ice-water and the product is taken up in methylene chloride. The extract is washed successively with dilute hydrochloric acid, saturated sodium bicarbonate solution and water, dried over sodium sulfate and evaporated. The crude product is chromatographed on a column of 300 g. of silica gel with toluene/5% acetone (v/v). The fractions which are pure according to thin-layer chromatography are combined and evaporated. The residue is dissolved in hexane, filtered hot with active carbon and recrystallized. The crystallizate is dried in vacuo overnight. There is obtained trans-4-[5-(p-n-heptylphenyl)-2-pyrimidinyl]cyclohexane carbonitrile; melting point 83.5° C., clearing point 160° C.

Workup

  1. washThe extract is washed successively with dilute hydrochloric acid, saturated sodium bicarbonate solution and water
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe crude product is chromatographed on a column of 300 g
  5. customevaporated
  6. dissolutionThe residue is dissolved in hexane
  7. filtrationfiltered hot with active carbon
  8. customrecrystallized
  9. customThe crystallizate is dried in vacuo overnight

Sources & evidence

ORD record
ord-a61672e9d4e94c1f9e230559094d52de
Source dataset
uspto-grants-1981_06
Patent number
US04273929

Reaction notes

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