Pyridine → HCID 178444376, compound

HRID 2166809Notes

Reaction equation

HRID 2166809 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:28]3[CH:36]=[CH:35][C:31]([C:32]([NH2:34])=O)=[CH:30][CH: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:28]3[CH:36]=[CH:35][C:31]([C:32]#[N:34])=[CH:30][CH:29]=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 178444377HCID 178444377, compound

Product 1

HCID 178444376HCID 178444376, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

9.5 Ml. of benzenesulfonyl chloride are added dropwise while stirring to a suspension of 17.2 g. of crude trans-p-[5-(4-n-pentylcyclohexyl)-2-pyrimidinyl]benzamide in 150 ml. of pyridine. The mixture is then warmed to 55° C. for 6 hours in an oil-bath. The mixture is poured into 500 ml. of ice-cold 0.5-N hydrochloric acid and the product is taken up in methylene chloride. The extract is washed three times with 200 ml. of 3-N hydrochloric acid each time, then with 100 ml. of saturated sodium bicarbonate solution and with water, dried over sodium sulfate and evaporated. The crude product is chromatographed on a column of 600 g. of silica gel with toluene/5% acetone (v/v). The fractions which are pure according to thin-layer chromatography are dissolved in hexane, filtered hot with active carbon and recrystallized. There is obtained trans-p-[5-(4-n-pentylcyclohexyl)-2-pyrimidinyl]benzonitrile; melting point 100.5° C., clearing point 231° C.

Workup

  1. additionThe mixture is poured into 500 ml
  2. washThe extract is washed three times with 200 ml
  3. dry with materialof saturated sodium bicarbonate solution and with water, dried over sodium sulfate
  4. customevaporated
  5. customThe crude product is chromatographed on a column of 600 g
  6. dissolutionare dissolved in hexane
  7. filtrationfiltered hot with active carbon
  8. customrecrystallized

Sources & evidence

ORD record
ord-0d7669124e414980a82c234609f3d901
Source dataset
uspto-grants-1983_06
Patent number
US04389329

Reaction notes

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