Hydrochloric Acid → HCID 178444380, compound

HRID 1463005Notes

Reaction equation

HRID 1463005 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:13]=[N:14][C:15]([CH:18]=O)=[N:16][CH:17]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].Cl.[NH2:21]O.C1(S(Cl)(=O)=O)C=CC=CC=1.Cl>N1C=CC=CC=1>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:13]=[N:14][C:15]([C:18]#[N:21])=[N:16][CH:17]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 178444381HCID 178444381, compound

Product 1

HCID 178444380HCID 178444380, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

9.0 g of trans-5-(4-pentylcyclohexyl)-2-pyrimidinecarboxaldehyde are dissolved in 150 ml of pyridine under a nitrogen atmosphere, treated with 3.9 g of hydroxylamine hydrochloride and stirred at room temperature for 2 hours. Thereafter, the mixture is treated with 18.3 g of benzenesulphonyl chloride, the temperature rising to about 50° C. Subsequently, the mixture is stirred at a bath temperature of 70° C. for 6 hours, then cooled, poured into 500 ml of ice/water and 100 ml of concentrated hydrochloric acid and extracted with ether. The extract is washed with dilute hydrochloric acid, washed neutral with water, dried over sodium sulphate and evaporated. The crude product obtained is chromatographed on a column of 275 g of silica gel with hexane/20% ether. The almost pure fractions (in accordance with thin-layer chromatography) are combined and recrystallized three times from hexane. There is obtained pure trans-5-(4-pentylcyclohexyl)-2-pyrimidinecarbonitrile; m.p. 83.5° C.

Workup

  1. customrising to about 50° C
  2. stirringSubsequently, the mixture is stirred at a bath temperature of 70° C. for 6 hours
  3. temperaturecooled
  4. extractionextracted with ether
  5. washThe extract is washed with dilute hydrochloric acid
  6. washwashed neutral with water
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. customThe crude product obtained
  10. customis chromatographed on a column of 275 g of silica gel with hexane/20% ether
  11. customrecrystallized three times from hexane

Sources & evidence

ORD record
ord-c52e34736fe74f95aab3e6d372924348
Source dataset
uspto-grants-1984_07
Patent number
US04462923

Reaction notes

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