Hydrochloric Acid → HCID 20496460, compound

HRID 1074384Notes

Reaction equation

HRID 1074384 reaction equation
[CH2:1]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:16]([NH2:18])=O)[CH:12]=2)[CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C1(S(Cl)(=O)=O)C=CC=CC=1.Cl>N1C=CC=CC=1>[CH2:1]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:16]#[N:18])[CH:12]=2)[CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 20450641HCID 20450641, compound

Product 1

HCID 20496460HCID 20496460, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.605 g of 2-pentyl-1,2,3,4-tetrahydro-naphthalene-6-carboxamide are suspended in 40 ml of absolute pyridine and treated with 2.86 g of benzenesulfonyl chloride while stirring. The solution, which becomes clear, is left to stand at room temperature overnight, the poured into a mixture of 50 g of ice and 40 ml of concentrated hydrochloric acid and exhaustively extracted with dichloromethane. The organic phases are washed neutral with water, dried over sodium sulfate and the solvent is removed by evaporation in vacuo. There are obtained 2.390 g of crude 2-pentyl-1,2,3,4-tetrahydronaphthalene-6-carbonitrile as a yellowish oil which, for purification, is chromatographed on 90 g of silica gel. Elution with hexane/toluene (1:1) and toluene yields 2.35 g of a yellowish oil which crystallizes at -10° C. It is crystallized up to a constant melting point from a small amount of ethanol by cooling the solution to -10° C. and separating the mother liquor from the precipitated crystals, for example, by decantation, pipetting or filtration through a cooled filter. Subsequently, it is dried up to constant weight in a high vacuum (0.01 mbar). There are obtained colorless crystals, or a colorless oil, of 2-pentyl-1,2,3,4-tetrahydronaphthalene-6-carbonitrile; m.p. 18.2° C.

Workup

  1. waitis left
  2. extractionexhaustively extracted with dichloromethane
  3. washThe organic phases are washed neutral with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is removed by evaporation in vacuo

Sources & evidence

ORD record
ord-5c0e78c974724143b32d05c80a1ec8d4
Source dataset
uspto-grants-1983_07
Patent number
US04391731

Reaction notes

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